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140 reactions in Reaxys
2018-06-02 11h:29m:47s (UTC)
O
O
1. Query
HO
O
Search as: Product, As drawn, No mixtures ) AND (RX.PXRN=150206))
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O O
O
O
HO O
O
Rx-ID: 123324 View in Reaxys 1/140 Yield
Conditions & References With sodium chlorite, sodium dihydrogenphosphate, dihydrogen peroxide in water, acetonitrile, Cooling with ice Dam, Johan Hygum; Madsen, Robert; European Journal of Organic Chemistry; nb. 27; (2009); p. 4666 - 4673 View in Reaxys With NH-pyrazole, air, sodium hydride in tetrahydrofuran, Time= 7h, Ambient temperature Ohta, Shunsaku; Tachi, Takao; Okamoto, Masao; Synthesis; nb. 4; (1983); p. 291 - 293 View in Reaxys With 4H3N*4H(1+)*CuMo6O18(OH)6(4-), water, oxygen, sodium carbonate, Time= 12h, T= 50 °C , p= 760.051Torr , Catalytic behavior, Reagent/catalyst, Temperature Yu, Han; Ru, Shi; Zhai, Yongyan; Dai, Guoyong; Han, Sheng; Wei, Yongge; ChemCatChem; vol. 10; nb. 6; (2018); p. 1253 - 1257 View in Reaxys With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate, 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2a]pyrimidine in acetonitrile, T= 20 °C Zhao, Junfeng; Mueck-Lichtenfeld, Christian; Studer, Armido; Advanced Synthesis and Catalysis; vol. 355; nb. 6; (2013); p. 1098 - 1106 View in Reaxys With sodium chlorite, sodium dihydrogenphosphate in water, tert-butyl alcohol, Time= 2h, T= 20 °C , Pinnick oxidation Ganton, Michael D.; Kerr, Michael A.; Organic Letters; vol. 7; nb. 21; (2005); p. 4777 - 4779 View in Reaxys With potassium hydroxide, sodium tetrahydroborate, air, 10 wt. % palladium on activated carbon in methanol, Time= 4h, T= 20 °C Lim, Minkyung; Yoon, Cheol Min; An, Gwangil; Rhee, Hakjune; Tetrahedron Letters; vol. 48; nb. 22; (2007); p. 3835 - 3839 View in Reaxys With dihydrogen peroxide, potassium hydroxide in methanol, water, Time= 0.5h, T= 65 °C Huang, Xiaobo; Zhang, Bingchuan; Xu, Hui; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 18; (2017); p. 4336 4340 View in Reaxys 70a.1 :Step 1: Benzo [d] [1, 3] DIOXOLE-5-CARBOXYLIC acid (255a) [0407] To a stirred solution of benzo [d] [1, 3] dioxole-5-carbaldehyde (254a, 2 g, 13.3 MMOL), NA2H2PO4 (6.38 g, 53.2 MMOL), and 2-methyl-2-butene (9.85 mL, 93.1 MMOL) in t-BuOH (41 mL) and water (17 mL) was added sodium CHLORITE (7.19 g, 79.9 MMOL). The resulting reaction mixture was stirred for 2 hours at room temperature. Water (100 mL) and 1M HCI (25 mL) were added and the mixture was extracted with EtOAc (2 x 50 mL). The organic phase was separated, dried with sodium sulfate and evaporated under reduced pressure. The resulting solid was triturated with EtOAc (20 mL) to yield the title compound 255a as a white solid (1.9 g, 86percent yield NMR: (DMSO) 8 12.72 (br s, 1H), 7.53-7. 50 (m, 1H), 7.34-7. 32 (m, 1H), 6.99-6. 95 (m, 1H), 6.10 (s, 2H). Stage 1: With sodium chlorite, Na2H2PO4, water in 2-methyl-but-2-ene, tert-butyl alcohol, Time= 2h, T= 20 °C Stage 2: With hydrogenchloride, water in 2-methyl-but-2-ene, tert-butyl alcohol Patent; METHYLGENE, INC.; WO2005/30704; (2005); (A1) English View in Reaxys With chromium(VI) oxide, acetic acid, Time= 1h, Ambient temperature Kuo; Lin; Chemical and Pharmaceutical Bulletin; vol. 41; nb. 9; (1993); p. 1507 - 1512
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View in Reaxys With barium permanganate in acetonitrile, Time= 15h, Heating Firouzabadi; Seddighi; Mottaghineiad; Bolourchian; Tetrahedron; vol. 46; nb. 19; (1990); p. 6869 - 6878 View in Reaxys With C19H26ClIrN3O(1+)*Cl(1-), sodium hydroxide in water, Time= 12h, T= 80 °C , Reagent/catalyst, chemoselective reaction Yang, Zhanhui; Luo, Renshi; Zhu, Zhongpeng; Yang, Xuerong; Tang, Weiping; Organometallics; vol. 36; nb. 21; (2017); p. 4095 - 4098 View in Reaxys With copper acetylacetonate, oxygen, sodium hydroxide, 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene in water, Time= 12h, T= 50 °C , p= 760.051Torr , Sealed tube, Reagent/catalyst Liu, Mingxin; Li, Chao-Jun; Angewandte Chemie - International Edition; vol. 55; nb. 36; (2016); p. 10806 - 10810; Angew. Chem.; vol. 128; (2016); p. 10964 - 10968,4 View in Reaxys With potassium permanganate in water, Time= 1h, T= 80 °C Buss, Antony D.; Warren, Stuart; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2307 - 2326 View in Reaxys With potassium permanganate, <2-(n-dodecylmethyl-tert-butylsiloxy)ethyl>trimethylammonium nitrate in water, benzene, Time= 2.5h, T= 50 - 55 °C Jaeger, David A.; Ward, Mary Darlene; Dutta, Aloke K.; Journal of Organic Chemistry; vol. 53; nb. 7; (1988); p. 1577 - 1580 View in Reaxys With barium manganate in dichloromethane, Time= 42h, Ambient temperature Srivastava, R.G.; Venkataramani, P.S.; Synthetic Communications; vol. 18; nb. l6-17; (1988); p. 2193 - 2200 View in Reaxys With potassium permanganate, <2-(n-dodecylmethyl-tert-butylsiloxy)ethyl>trimethylammonium nitrate, T= 50 - 60 °C Jaeger, David A.; Ward, Mary Darlene; Journal of Organic Chemistry; vol. 47; nb. 11; (1982); p. 2221 - 2223 View in Reaxys With potassium permanganate, 1-<3-(4-decyl-2-methyl-1,3-dioxolan-2-yl)propyl>-1-azoniabicyclo<2.2.2>octane chloride in water, Time= 2.5h, T= 50 - 60 °C , other surfactant, Product distribution Jaeger, David A.; Frey, Moira R.; Journal of Organic Chemistry; vol. 47; nb. 2; (1982); p. 311 - 315 View in Reaxys With potassium hydroxide, T= 20 °C Barger; Journal of the Chemical Society; vol. 93; (1908); p. 565; Chemische Berichte; vol. 42; (1909); p. 763 View in Reaxys With potassium hydroxide Decker; Koch; Chemische Berichte; vol. 38; (1905); p. 1741 View in Reaxys Fittig; Mielck; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 52,54; Justus Liebigs Annalen der Chemie; vol. 172; (1874); p. 140,152 View in Reaxys With potassium permanganate Fittig; Mielck; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 52,54; Justus Liebigs Annalen der Chemie; vol. 172; (1874); p. 140,152 View in Reaxys With potassium permanganate
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Organic Syntheses; View in Reaxys Cattelain; Bulletin de la Societe Chimique de France; vol. <4> 39; (1926); p. 1188 View in Reaxys With sodium hydroxide, ethanol Orr; Robinson; Williams; Journal of the Chemical Society; vol. 111; (1917); p. 948 View in Reaxys With permanganate(VII) ion Bogert; Elder; Journal of the American Chemical Society; vol. 51; (1929); p. 536 View in Reaxys Shriner; Kleiderer; Organic Syntheses; vol. Coll. Vol. II; (1943); p. 538 View in Reaxys With alkaline aqueous potassium hypobromite solution Slotta; Haberland; Angewandte Chemie; vol. 46; (1933); p. 766,770, 771 View in Reaxys With sodium hydroxide, dihydrogen peroxide Dobrowsky; Monatshefte fuer Chemie; vol. 86; (1955); p. 325 View in Reaxys With potassium hydroxide, water, bromine, unter Durchleiten von Luft van Linge; Recueil des Travaux Chimiques des Pays-Bas; vol. 16; (1897); p. 45 View in Reaxys With potassium permanganate Anxin, Wu; Mingyi, Wang; Yonghong, Gan; Xinfu, Pan; Journal of Chemical Research - Part S; nb. 3; (1998); p. 136 - 137 View in Reaxys With heterologously expressed p-anisaldehyde dehydrogenase in escherichia coli, Enzymatic reaction, Kinetics, Concentration Han, Dongfei; Kurusarttra, Somwang; Ryu, Ji-Young; Kanaly, Robert A.; Hur, Hor-Gil; Journal of Agricultural and Food Chemistry; vol. 60; nb. 48; (2012); p. 11972 - 11979 View in Reaxys O O HO
O
O
O
HO O
O
O
Rx-ID: 11100434 View in Reaxys 2/140 Yield 59 %
Conditions & References With 2.9-dimethyl-1,10-phenanthroline, oxygen, sodium hydrogencarbonate, gold(I) chloride in water, Time= 24h, T= 100 °C , p= 38002.6Torr Li, Huanrong; Guan, Bingtao; Wang, Wenjin; Xing, Dong; Fang, Zhao; Wan, Xiaobing; Yang, Liping; Shi, Zhangjie; Tetrahedron; vol. 63; nb. 35; (2007); p. 8430 - 8434 View in Reaxys
43 %
General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 °C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57percent) as a pale yellow solid.
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With Iron(III) nitrate nonahydrate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, potassium chloride, oxygen in 1,2-dichloro-ethane, Time= 48h, T= 25 °C , Schlenk technique Jiang, Xingguo; Ma, Shengming; Synthesis (Germany); vol. 50; nb. 8; (2018); p. 1629 - 1639 View in Reaxys O O
O
O
HO
O
HO O
O O
Rx-ID: 123317 View in Reaxys 3/140 Yield
Conditions & References With sodium hydroxide Decker; Koch; Chemische Berichte; vol. 38; (1905); p. 1741 View in Reaxys
82 % Chromat.
With barium dihydroxide, formaldehyd, Time= 0.025h, T= 100 - 110 °C , Irradiation Varma, Rajender S.; Naicker, Kannan P.; Liesen, Per J.; Tetrahedron Letters; vol. 39; nb. 46; (1998); p. 8437 - 8440 View in Reaxys
6 %Spectr.
With C19H26ClIrN3O(1+)*Cl(1-), sodium hydroxide in water, Time= 12h, T= 80 °C , Reagent/catalyst, Temperature, chemoselective reaction Yang, Zhanhui; Luo, Renshi; Zhu, Zhongpeng; Yang, Xuerong; Tang, Weiping; Organometallics; vol. 36; nb. 21; (2017); p. 4095 - 4098 View in Reaxys O
Br
O O
O
O HO
O
O
Rx-ID: 1728450 View in Reaxys 4/140 Yield
Conditions & References With diethylzinc, palladium diacetate, tert-butyl XPhos in hexanes, N,N-dimethyl acetamide, T= 40 °C , p= 7600.51Torr , Automated synthesizer Correa, Arkaitz; Martin, Ruben; Journal of the American Chemical Society; vol. 131; nb. 44; (2009); p. 15974 - 15975 View in Reaxys With magnesium Podda, G.; Maccioni, A.; Fadda, A.; Daolio, S.; Traldi, P.; Vecchi, E.; Organic Mass Spectrometry; vol. 18; nb. 7; (1983); p. 318 - 320 View in Reaxys With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine, (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate, palladium diacetate, caesium carbonate, N-ethyl-N,N-diisopropylamine in N,N-dimethyl acetamide, Time= 6h, T= 20 °C , p= 760.051Torr , Irradiation Shimomaki, Katsuya; Murata, Kei; Martin, Ruben; Iwasawa, Nobuharu; Journal of the American Chemical Society; vol. 139; nb. 28; (2017); p. 9467 - 9470 View in Reaxys
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O O O
HO HO O
O
Rx-ID: 1760411 View in Reaxys 5/140 Yield
Conditions & References With NH-pyrazole, sodium hydride in tetrahydrofuran, Time= 20h, Ambient temperature Ohta, Shunsaku; Tachi, Takao; Okamoto, Masao; Synthesis; nb. 4; (1983); p. 291 - 293 View in Reaxys With barium permanganate in acetonitrile, Time= 18h, Heating Firouzabadi; Seddighi; Mottaghineiad; Bolourchian; Tetrahedron; vol. 46; nb. 19; (1990); p. 6869 - 6878 View in Reaxys With dihydrogen peroxide in water, toluene, Time= 4h, T= 20 - 85 °C Hu, Yu Lin; Ma, Xiao Yun; Ge, Qiang; Lu, Ming; Acta Chimica Slovenica; vol. 57; nb. 4; (2010); p. 927 - 930 View in Reaxys With [Rh(1,3,4,5-tetramethylimidazole-2-ylidene)(trop2NH)][trifluoromethanesulfonate], potassium tert-butylate, dinitrogen monoxide in tetrahydrofuran, toluene, T= 50 °C , p= 750.075Torr , Schlenk technique Gianetti, Thomas L.; Annen, Samuel P.; Santiso-Quinones, Gustavo; Reiher, Markus; Driess, Matthias; Grützmacher, Hansjörg; Angewandte Chemie - International Edition; vol. 55; nb. 5; (2016); p. 1854 - 1858; Angew. Chem.; vol. 128; nb. 5; (2015); p. 1886 - 1890,5 View in Reaxys With sodium hydroxide, osmium(VIII) oxide, sulfuric acid, potassium hexacyanoferrate(III) in water, Time= 3h, Ambient temperature Bailey, Alan J.; Bhowon, Minu G.; Griffith, William P.; Shoair, Abdel G. F.; White, Andrew J. P.; Williams, David J.; Journal of the Chemical Society - Dalton Transactions; nb. 18; (1997); p. 3245 - 3250 View in Reaxys With C32H25Cl2N6O2Rh2 (1+)*Cl(1-), sodium hydroxide in water, Time= 12h, T= 100 °C , Sealed tube, Green chemistry Wang, Xuewei; Wang, Chao; Liu, Yuxuan; Xiao, Jianliang; Green Chemistry; vol. 18; nb. 17; (2016); p. 4605 - 4610 View in Reaxys With oxygen, sodium carbonate in water, tert-butyl alcohol, Time= 0.533333h, T= 120 °C , p= 52505.3Torr , Flow reactor, Green chemistry Osako, Takao; Torii, Kaoru; Uozumi, Yasuhiro; RSC Advances; vol. 5; nb. 4; (2015); p. 2647 - 2654 View in Reaxys Stage 1: With potassium permanganate, disodium hydrogenphosphate in methanol, water, T= 25 °C , Continuous flow conditions, Sonication Stage 2: With hydrogenchloride, sodium thiosulfate, sodium chloride in methanol, water, ethyl acetate Sedelmeier, Joerg; Ley, Steven V.; Baxendale, Ian R.; Baumann, Marcus; Organic Letters; vol. 12; nb. 16; (2010); p. 3618 3621 View in Reaxys With sodium tetrahydroborate, 1% Pd/C, water, potassium hydroxide in methanol, Time= 17h, T= 20 °C , In air An, Gwangil; Ahn, Hyunseok; De Castro, Kathlia A.; Rhee, Hakjune; Synthesis; nb. 3; (2010); p. 477 - 485; Art.No: F19009SS View in Reaxys With sodium periodate, <Ru(OH)2<IO5(OH)>2>(6-), sulfuric acid, 1) aq. KOH, rt, 3 h, Yield given. Multistep reaction
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Dengel, Andrew C.; El-Hendawy, Ahmed M.; Griffith, William P.; Mostafa, Sahar I.; Williams, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 24; (1992); p. 3489 - 3496 View in Reaxys With water, potassium carbonate, T= 80 °C , Catalytic behavior Vessally, Esmail; Ghasemisarabbadeih, Mostafa; Ekhteyari, Zeynab; Hosseinzadeh-Khanmiri, Rahim; Ghorbani-Kalhor, Ebrahim; Ejlali, Ladan; RSC Advances; vol. 6; nb. 108; (2016); p. 106769 - 106777 View in Reaxys With oxygen, potassium hydroxide in methanol, water, Time= 4h, T= 50 °C , p= 760.051Torr Ahmed, Maaz S.; Mannel, David S.; Root, Thatcher W.; Stahl, Shannon S.; Organic Process Research and Development; vol. 21; nb. 9; (2017); p. 1388 - 1393 View in Reaxys O
O
O
O
HO
O
O
O
Rx-ID: 9454912 View in Reaxys 6/140 Yield
Conditions & References With sodium hydroxide in tetrahydrofuran, methanol, T= 40 °C , Inert atmosphere Giacomini, Daria; Musumeci, Rosario; Galletti, Paola; Martelli, Giulia; Assennato, Lorenzo; Sacchetti, Gianni; Guerrini, Alessandra; Calaresu, Enrico; Martinelli, Marianna; Cocuzza, Clementina; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 604 - 614 View in Reaxys With potassium hydroxide in methanol, Time= 1h, T= 35 °C Khurana, Jitender M.; Chauhan, Sushma; Bansal, Geeti; Monatshefte fur Chemie; vol. 135; nb. 1; (2004); p. 83 - 87 View in Reaxys O
F (v3) (v3)
(v3) (v3)
O O
O O
O
(v6) (v6)
Co
Co
O
O O
S
O
HO
O
O
O
F
O
F
(v3)
(v3)
F
O
O
F
Rx-ID: 44608491 View in Reaxys 7/140 Yield
Conditions & References With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2, potassium acetate in 1,4-dioxane, water, Time= 16h, T= 20 °C , Schlenk technique, Inert atmosphere, chemoselective reaction Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Shashikanth, Sheena; Advanced Synthesis and Catalysis; vol. 359; nb. 3; (2017); p. 419 - 425 View in Reaxys O (v3) (v3)
(v3) (v3)
O O
O
F
Co
S O
O O O
F
O O (v6) (v6)
Co
(v3)
F
O
O
HO
O
O
O
O
(v3)
Rx-ID: 44608558 View in Reaxys 8/140 Yield
Conditions & References With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2, potassium acetate in 1,4-dioxane, water, Time= 16h, T= 20 °C , Schlenk technique, Inert atmosphere, chemoselective reaction
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Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Shashikanth, Sheena; Advanced Synthesis and Catalysis; vol. 359; nb. 3; (2017); p. 419 - 425 View in Reaxys O HO
O
O HO O
O
Rx-ID: 44608611 View in Reaxys 9/140 Yield
Conditions & References Reaction Steps: 2 1: triethylamine / dichloromethane / 0 - 20 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane; water / 16 h / 20 °C / Schlenk technique; Inert atmosphere With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2, potassium acetate, triethylamine in 1,4-dioxane, dichloromethane, water Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Shashikanth, Sheena; Advanced Synthesis and Catalysis; vol. 359; nb. 3; (2017); p. 419 - 425 View in Reaxys O
O N
O
O HO
N
O
O
Rx-ID: 44816340 View in Reaxys 10/140 Yield
Conditions & References With sodium hydroxide in tetrahydrofuran, water, Time= 12h, T= 25 °C Ovian, John M.; Kelly, Christopher B.; Pistritto, Vincent A.; Leadbeater, Nicholas E.; Organic Letters; vol. 19; nb. 6; (2017); p. 1286 - 1289 View in Reaxys O
Br
O
O O
O
O
HO
O
O
O
Rx-ID: 45962089 View in Reaxys 11/140 Yield 6 %Spectr.
Conditions & References With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine, (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate, palladium diacetate, caesium carbonate, N-ethyl-N,N-diisopropylamine in N,N-dimethyl acetamide, Time= 6h, T= 20 °C , p= 760.051Torr , Irradiation, Reagent/catalyst, Solvent Shimomaki, Katsuya; Murata, Kei; Martin, Ruben; Iwasawa, Nobuharu; Journal of the American Chemical Society; vol. 139; nb. 28; (2017); p. 9467 - 9470 View in Reaxys O
HO
O HO O HO
O
Rx-ID: 46128998 View in Reaxys 12/140
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Yield
Conditions & References Reaction Steps: 2 1: potassium carbonate / dichloromethane / 4 h / 105 °C 2: dihydrogen peroxide; potassium hydroxide / water; methanol / 0.5 h / 65 °C With dihydrogen peroxide, potassium carbonate, potassium hydroxide in methanol, dichloromethane, water Huang, Xiaobo; Zhang, Bingchuan; Xu, Hui; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 18; (2017); p. 4336 4340 View in Reaxys OH
O
B
O
O
HO
HO
C N
O
O
Rx-ID: 46326205 View in Reaxys 13/140 Yield
Conditions & References Stage 1: With copper diacetate, palladium diacetate in N,N-dimethyl-formamide, Time= 24h, T= 100 °C , Molecular sieve, Sealed tube Stage 2: With water in N,N-dimethyl-formamide, Molecular sieve, Sealed tube Chen, Zhen-Bang; Liu, Kui; Zhang, Fang-Ling; Yuan, Qing; Zhu, Yong-Ming; Organic and Biomolecular Chemistry; vol. 15; nb. 38; (2017); p. 8078 - 8083 View in Reaxys O OH
O
O
HO OH
O
O
Rx-ID: 46352182 View in Reaxys 14/140 Yield
Conditions & References Reaction Steps: 2 1: potassium carbonate / N,N-dimethyl-formamide / 110 °C / Inert atmosphere 2: sodium hydroxide / methanol; tetrahydrofuran / 40 °C / Inert atmosphere With potassium carbonate, sodium hydroxide in tetrahydrofuran, methanol, N,N-dimethyl-formamide Giacomini, Daria; Musumeci, Rosario; Galletti, Paola; Martelli, Giulia; Assennato, Lorenzo; Sacchetti, Gianni; Guerrini, Alessandra; Calaresu, Enrico; Martinelli, Marianna; Cocuzza, Clementina; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 604 - 614 View in Reaxys
O O
O
O O
HO
S O
O O
Rx-ID: 38878308 View in Reaxys 15/140 Yield
Conditions & References A representative synthetic procedure of skeletons 3 and 5 is as follows General procedure: Ce(NH4)2(NO3)6 (CAN, 274 mg, 0.5 mmol) was added to a solution of β-ketosulfones 2 (0.5 mmol) in MeCN (10 mL) at rt. The reaction mixture was stirred at 50 oC for 4 h, cooled to rt, and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Products 3 and 5 were isolated and recrystalised from EtOAc and THF.
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With ammonium cerium (IV) nitrate, oxygen in acetonitrile, Time= 4h, T= 20 - 50 °C Chang, Meng-Yang; Tsai, Chung-Yu; Tetrahedron Letters; vol. 55; nb. 40; (2014); p. 5548 - 5550 View in Reaxys OH O
O
B
O
O
O
HO
HO
O
O
O
Rx-ID: 38903036 View in Reaxys 16/140 Yield
Conditions & References 2.1 Typical procedure for thesynthesis of aromatic carboxylic acids from arylboronic acids and acetylacetate: General procedure: Phenylboronic acid (0.12 g, 1.0 mmol)acetyl acetate (650mg, 5.0 mmol)CuI (19 mg, 10 molpercent)K2CO3(0.28 g, 2.0 mmol) were dissolved in DMSO (5 mL, anhydrous). The solution was stirred at 100 °C under nitrogen atmosphere for 24h and then cooled and the solution was poured into HCl (40 mL, 1 mol/L). The mixture was extracted with CH2Cl2 (40 mL). Then, the solution was washed with HCl (40 mL, 1 mol/l), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt 20:1) to give the desired product 3a(117 mg, 96percent) as a white solid. With copper(l) iodide, potassium carbonate in dimethyl sulfoxide, Time= 24h, T= 100 °C , Inert atmosphere Zheng, Rui; Zhou, Qizhong; Gu, Haining; Jiang, Huajiang; Wu, Jiashou; Jin, Zhengneng; Han, Deman; Dai, Guoliang; Chen, Rener; Tetrahedron Letters; vol. 55; nb. 41; (2014); p. 5671 - 5675 View in Reaxys O
O
O
O
HO
Cl
O
O
Rx-ID: 36740008 View in Reaxys 17/140 Yield
Conditions & References General procedure: The solvents were purified as previously described.29 The piperonyloyl chloride (1, Aldrich, 98percent) was used as received. The kinetic experiments were performed by allowing a conductivity cell containing 5.0 mL of solvent to equilibrate, with stirring, in a constant-temperature water bath. Then, a 10 μL portion of a 1.0 mol dm−3 stock solution of 1 in acetonitrile was added. The monitoring of the conductivity increases with time and the rate constant calculations were conducted as previously reported.29 Multiple regression analyses were performed using commercially available packages.29 The solvolysis products, (ester and acid), were determinedvia the HPLC analysis, as reported previously;6(b),30 the product selectivities, (S), were calculated using Eq. (3). The S values were calculated from the observed peak area ratios of the ester and acid; S values were divided by the appropriate response factor. For the response calibrations, the area ratios from the solvolysis of 1 in pure alcohol and in 40percent acetonitrile-water mixtures were used. The eluent was a 60percent methanol-water mixture; the flow rate was adjusted to 1 mL min−1. The HPLC system was a Hewlett-Packard 1050 Series instrument, with 250 × 4 mm Spherisorb ODS reversed columns. With water in acetone, acetonitrile, T= 25 °C , Kinetics Oh, Hyunjung; Choi, Hojune; Park, Jong Keun; Yang, Kiyull; Koo, In Sun; Bulletin of the Korean Chemical Society; vol. 34; nb. 9; (2013); p. 2697 - 2701 View in Reaxys O
O
O
O
O
HO
HO
Cl
O O
O
O
O
Rx-ID: 36740009 View in Reaxys 18/140
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Yield
Conditions & References General procedure: The solvents were purified as previously described.29 The piperonyloyl chloride (1, Aldrich, 98percent) was used as received. The kinetic experiments were performed by allowing a conductivity cell containing 5.0 mL of solvent to equilibrate, with stirring, in a constant-temperature water bath. Then, a 10 μL portion of a 1.0 mol dm−3 stock solution of 1 in acetonitrile was added. The monitoring of the conductivity increases with time and the rate constant calculations were conducted as previously reported.29 Multiple regression analyses were performed using commercially available packages.29 The solvolysis products, (ester and acid), were determinedvia the HPLC analysis, as reported previously;6(b),30 the product selectivities, (S), were calculated using Eq. (3). The S values were calculated from the observed peak area ratios of the ester and acid; S values were divided by the appropriate response factor. For the response calibrations, the area ratios from the solvolysis of 1 in pure alcohol and in 40percent acetonitrile-water mixtures were used. The eluent was a 60percent methanol-water mixture; the flow rate was adjusted to 1 mL min−1. The HPLC system was a Hewlett-Packard 1050 Series instrument, with 250 × 4 mm Spherisorb ODS reversed columns. With water in acetonitrile, T= 25 °C , Kinetics Oh, Hyunjung; Choi, Hojune; Park, Jong Keun; Yang, Kiyull; Koo, In Sun; Bulletin of the Korean Chemical Society; vol. 34; nb. 9; (2013); p. 2697 - 2701 View in Reaxys O
O
O
O
OH
Cl
O
O
HO
O
O
O
O
Rx-ID: 36740010 View in Reaxys 19/140 Yield
Conditions & References General procedure: The solvents were purified as previously described.29 The piperonyloyl chloride (1, Aldrich, 98percent) was used as received. The kinetic experiments were performed by allowing a conductivity cell containing 5.0 mL of solvent to equilibrate, with stirring, in a constant-temperature water bath. Then, a 10 μL portion of a 1.0 mol dm−3 stock solution of 1 in acetonitrile was added. The monitoring of the conductivity increases with time and the rate constant calculations were conducted as previously reported.29 Multiple regression analyses were performed using commercially available packages.29 The solvolysis products, (ester and acid), were determinedvia the HPLC analysis, as reported previously;6(b),30 the product selectivities, (S), were calculated using Eq. (3). The S values were calculated from the observed peak area ratios of the ester and acid; S values were divided by the appropriate response factor. For the response calibrations, the area ratios from the solvolysis of 1 in pure alcohol and in 40percent acetonitrile-water mixtures were used. The eluent was a 60percent methanol-water mixture; the flow rate was adjusted to 1 mL min−1. The HPLC system was a Hewlett-Packard 1050 Series instrument, with 250 × 4 mm Spherisorb ODS reversed columns. With water in acetonitrile, T= 25 °C , Kinetics Oh, Hyunjung; Choi, Hojune; Park, Jong Keun; Yang, Kiyull; Koo, In Sun; Bulletin of the Korean Chemical Society; vol. 34; nb. 9; (2013); p. 2697 - 2701 View in Reaxys O
O F
O F
F
O
O Cl
O
HO
HO
O F
F
F
O
O
O
Rx-ID: 36740011 View in Reaxys 20/140 Yield
Conditions & References General procedure: The solvents were purified as previously described.29 The piperonyloyl chloride (1, Aldrich, 98percent) was used as received. The kinetic experiments were performed by allowing a conductivity cell containing 5.0 mL of solvent to equilibrate, with stirring, in a constant-temperature water bath. Then, a 10 μL portion of a 1.0 mol dm−3 stock solution of 1 in acetonitrile was added. The monitoring of the conductivity increases with time and the rate constant calculations were conducted as previously reported.29 Multiple regression analyses were performed using commercially available packages.29 The solvolysis products, (ester and acid), were determinedvia the HPLC analysis, as reported previously;6(b),30 the product selectivities, (S), were calculated using Eq. (3). The S values were calculated from the observed peak area ratios of the ester and acid; S values were divided by the appropriate response factor. For the response calibrations, the area ratios from the solvolysis of 1 in pure
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alcohol and in 40percent acetonitrile-water mixtures were used. The eluent was a 60percent methanol-water mixture; the flow rate was adjusted to 1 mL min−1. The HPLC system was a Hewlett-Packard 1050 Series instrument, with 250 × 4 mm Spherisorb ODS reversed columns. With water in acetonitrile, T= 25 °C , Kinetics Oh, Hyunjung; Choi, Hojune; Park, Jong Keun; Yang, Kiyull; Koo, In Sun; Bulletin of the Korean Chemical Society; vol. 34; nb. 9; (2013); p. 2697 - 2701 View in Reaxys O O
O HO O
O
Rx-ID: 809021 View in Reaxys 21/140 Yield
Conditions & References With potassium permanganate Ciamician; Silber; Gazzetta Chimica Italiana; vol. 20; (1890); p. 571; Chemische Berichte; vol. 23; (1890); p. 1160 View in Reaxys With recombinant escherichia coli strain expressing trans-anethole oxygenase and p-anisaldehyde dehydrogenase, Enzymatic reaction, Kinetics, Concentration Han, Dongfei; Kurusarttra, Somwang; Ryu, Ji-Young; Kanaly, Robert A.; Hur, Hor-Gil; Journal of Agricultural and Food Chemistry; vol. 60; nb. 48; (2012); p. 11972 - 11979 View in Reaxys
O O O
B
O
O
O HO
O
O O
Rx-ID: 33406219 View in Reaxys 22/140 Yield
Conditions & References Stage 1: With potassium tert-butylate, silver(I) acetate, triphenylphosphine in 1,4-dioxane, Time= 8h, T= 100 °C , p= 15201Torr , Inert atmosphere, Autoclave Stage 2: With hydrogenchloride in tetrahydrofuran, water, Inert atmosphere Zhang, Xiao; Zhang, Wen-Zhen; Shi, Ling-Long; Guo, Chun-Xiao; Zhang, Ling-Ling; Lu, Xiao-Bing; Chemical Communications; vol. 48; nb. 50; (2012); p. 6292 - 6294 View in Reaxys O
O HO
O
Rx-ID: 5446381 View in Reaxys 23/140 Yield
Conditions & References 2 Patent; Intitut Català d'Investigació Química (ICIQ); EP2311788; (2011); (A1) English View in Reaxys Nakano,T. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1979); p. 2107 - 2112
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View in Reaxys Barton,D.H.R.; Jones,D.W.; Journal of the Chemical Society; (1965); p. 3563 - 3570 View in Reaxys Mc Evoy; Albright; Journal of Organic Chemistry; vol. 44; (1979); p. 4597,4600 View in Reaxys Pettit et al.; Journal of Medicinal and Pharmaceutical Chemistry; vol. 5; (1962); p. 800,804 View in Reaxys Lurik et al.; Pharmaceutical Chemistry Journal; vol. 5; nb. 8; (1971); p. 462; Khimiko-Farmatsevticheskii Zhurnal; vol. 5; nb. 8; (1971); p. 15 View in Reaxys Garg et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 16; (1978); p. 658 View in Reaxys Naik Satam; Bringi; Indian Journal of Chemistry; vol. 11; (1973); p. 209 View in Reaxys Bowden et al.; Australian Journal of Chemistry; vol. 25; (1972); p. 2659,2668 View in Reaxys Feugeas; Bulletin de la Societe Chimique de France; (1964); p. 1892 View in Reaxys Chikamoto; Agricultural and Biological Chemistry; vol. 28; (1964); p. 633,634 View in Reaxys Dallacker et al.; Monatshefte fuer Chemie; vol. 91; (1960); p. 1089,1096 View in Reaxys Rangaswami; Sastry; Proceedings - Indian Academy of Sciences, Section A; vol. 57; (1963); p. 135,137 View in Reaxys Resplandy; Mentzer; Annales Pharmaceutiques Francaises; vol. 18; (1960); p. 528,539 View in Reaxys Delle Monache et al.; Gazzetta Chimica Italiana; vol. 107; (1977); p. 403,405,406 View in Reaxys Lee; Tan; Journal of the Chemical Society; (1965); p. 2743,2747 View in Reaxys Ramaiah; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 71,74 View in Reaxys Baranova et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 47; (1974); p. 2751,2840,2841 View in Reaxys Filho et al.; Phytochemistry (Elsevier); vol. 12; (1973); p. 417,419 View in Reaxys Govindachari et al.; Indian Journal of Chemistry; vol. 10; (1972); p. 1120 View in Reaxys Anjaneyulu et al.; Tetrahedron; vol. 33; (1977); p. 133,135,139,140,143 View in Reaxys Kuraoka; Nippon Kagaku Zasshi; vol. 82; (1961); p. 50 View in Reaxys Scholz; Monatshefte fuer Chemie; vol. 110; (1979); p. 1471 View in Reaxys Narasimha Rao; Nigam; Riechstoffe und Aromen; vol. 22; (1972); p. 231,236 View in Reaxys Orphanos; Taurius; Canadian Journal of Chemistry; vol. 44; (1966); p. 1875,1877 View in Reaxys Among species of the compound of formula (III), the particularly preferred are 3,4-dimethoxybenzoic acid, 3-hydroxy-4-methoxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid, and 3,4-methylenedioxybenzoic acid. Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; EP839801; (1998); (A2) English View in Reaxys
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O
O
O
O
O O
O
O
O
O
HO O
Rx-ID: 36572379 View in Reaxys 24/140 Yield
Conditions & References
57 %, 12 %
With PhI(OAc)2/Al2O3, Time= 0.5h, T= 140 °C , Microwave irradiation Alvarez, Heiddy Marquez; Barbosa, Dayse P.; Fricks, Alini Tinoco; Aranda, Donato A. G.; Valdes, Ricardo H.; Antunes; Organic Process Research and Development; vol. 10; nb. 5; (2006); p. 941 - 943 View in Reaxys O O
O
O
O
HO O
O
O
Rx-ID: 36572380 View in Reaxys 25/140 Yield
Conditions & References
69 %
With PhI(OAc)2/Al2O3, Time= 0.0833333h, T= 110 °C , Microwave irradiation Alvarez, Heiddy Marquez; Barbosa, Dayse P.; Fricks, Alini Tinoco; Aranda, Donato A. G.; Valdes, Ricardo H.; Antunes; Organic Process Research and Development; vol. 10; nb. 5; (2006); p. 941 - 943 View in Reaxys O
O
OH
O
O
O
O
O
O
HO H
O
O
O
Rx-ID: 22848059 View in Reaxys 26/140 Yield 81 %Chromat.
Conditions & References Comparative Example 1 With peracetic acid in ethyl acetate, Time= 8h, T= 50 °C Patent; DAICEL CHEMICAL INDUSTRIES, Ltd.; EP1167365; (2002); (A1) English View in Reaxys O
N O
O HO
O
O
Rx-ID: 3483882 View in Reaxys 27/140 Yield
Conditions & References With phosphate buffer, Time= 24h, T= 30 °C , rhodococcus rhodocrous AJ270, pH 7.0 Meth-Cohn, Otto; Wang, Mei-Xiang; Tetrahedron Letters; vol. 36; nb. 52; (1995); p. 9561 - 9564 View in Reaxys With potassium phosphate buffer, Time= 24h, T= 30 °C , Rhodococcus sp. AJ270 cells
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Meth-Cohn, Otto; Wang, Mei-Xiang; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1997); p. 1099 - 1104 View in Reaxys With water, nitrile hydratase SP361, Time= 26h, T= 30 °C , in potassium phosphate buffer (pH = 7) Cohen, Mark A.; Sawden, Janette; Turner, Nicholas J.; Tetrahedron Letters; vol. 31; nb. 49; (1990); p. 7223 - 7226 View in Reaxys
H 2N
O
O
O HO
O O
O
O
Rx-ID: 24661105 View in Reaxys 28/140 Yield
Conditions & References 12 : 1,3-Benzodioxole-5-carboxylic acid, 6,6'-dithiobis-, dimethyl ester EXAMPLE 12 1,3-Benzodioxole-5-carboxylic acid, 6,6'-dithiobis-, dimethyl ester Prepared according to the procedure of Example 11 from 6-amino-benzo[1,3]dioxole-5-carboxylic acid methyl ester. Crystallized from methylene chloride/hexane; Analysis calc'd for C18 H14 O8 S2: C, 51.18; H, 3.34; Found: C, 51.04; H, 3.33. MS (CI) m/e 422. Patent; Warner-Lambert Company; US5599811; (1997); (A) English View in Reaxys O O
O
N
O
O
HO OH
O
O
O
Rx-ID: 3826376 View in Reaxys 29/140 Yield
Conditions & References
65 %
With sodium hypochlorite in acetonitrile, Time= 0.5h, Ambient temperature Khurana, Jitender Mohan; Ray, Abhijit; Sahoo, Prabhat Kumar; Bulletin of the Chemical Society of Japan; vol. 67; nb. 4; (1994); p. 1091 - 1093 View in Reaxys
O
O O
O
O
O O
O
O O
O
O
O
O HO O
O O O O
Rx-ID: 3824787 View in Reaxys 30/140 Yield
Conditions & References
15 %, 10 %, With chromium(VI) oxide, perchloric acid, acetonitrile, Time= 3h, T= 0 - 5 °C , Further byproducts given 14 % Kuo; Lin; Chemical and Pharmaceutical Bulletin; vol. 41; nb. 9; (1993); p. 1507 - 1512
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View in Reaxys O O
O O
O
HS
HO
S
O
O HO
Rx-ID: 1748714 View in Reaxys 31/140 Yield
Conditions & References With sodium hydride, 1) DMF, 2) 25 deg C, 12 h, Yield given. Multistep reaction. Yields of byproduct given Cassels, Bruce K.; Radetski, Claudemir; Rezende, Marcos Caroli; Recueil des Travaux Chimiques des Pays-Bas; vol. 111; nb. 10; (1992); p. 448 - 450 View in Reaxys O O
O
O
O
HO
S
O
O HO
Rx-ID: 1749281 View in Reaxys 32/140 Yield
Conditions & References With sodium hydride, 1) DMF, 2) 25 deg C, 12 h, Yield given. Multistep reaction. Yields of byproduct given Cassels, Bruce K.; Radetski, Claudemir; Rezende, Marcos Caroli; Recueil des Travaux Chimiques des Pays-Bas; vol. 111; nb. 10; (1992); p. 448 - 450 View in Reaxys
O
HS
O O
O
O
O
O
O
HO
S
O
O
Rx-ID: 1846275 View in Reaxys 33/140 Yield
Conditions & References With sodium hydride, 1) DMF, 2) rt, 2 h, Yield given. Multistep reaction. Yields of byproduct given Cassels, Bruce K.; Radetski, Claudemir; Rezende, Marcos Caroli; Recueil des Travaux Chimiques des Pays-Bas; vol. 111; nb. 10; (1992); p. 448 - 450 View in Reaxys O
HS
O O
O
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HO
O
O
O
HO S
O
O O
Rx-ID: 1955772 View in Reaxys 34/140 Yield
Conditions & References With sodium hydride, 1) DMF, 2) 25 deg C, 12 h, Yield given. Multistep reaction. Yields of byproduct given Cassels, Bruce K.; Radetski, Claudemir; Rezende, Marcos Caroli; Recueil des Travaux Chimiques des Pays-Bas; vol. 111; nb. 10; (1992); p. 448 - 450 View in Reaxys HO
O
O
O
O
O
HO
O
S O
O
O O
Rx-ID: 1955783 View in Reaxys 35/140 Yield
Conditions & References With sodium hydride, 1) DMF, 2) 25 deg C, 12 h, Yield given. Multistep reaction. Yields of byproduct given Cassels, Bruce K.; Radetski, Claudemir; Rezende, Marcos Caroli; Recueil des Travaux Chimiques des Pays-Bas; vol. 111; nb. 10; (1992); p. 448 - 450 View in Reaxys
O Si
O HO
O HO
O O
Rx-ID: 2830715 View in Reaxys 36/140 Yield
Conditions & References With dimethylsulfide, ozone, 1) CH2Cl2, -78 deg C, 2 min, Yield given. Multistep reaction Linderman, Russell J.; Chen, Kangyi; Tetrahedron Letters; vol. 33; nb. 45; (1992); p. 6767 - 6770 View in Reaxys
O
O
O
O O
HO
O S
O
O
O O
Rx-ID: 3215572 View in Reaxys 37/140 Yield
Conditions & References With sodium hydride, 1) DMF, 2) rt, 2 h, Yield given. Multistep reaction. Yields of byproduct given Cassels, Bruce K.; Radetski, Claudemir; Rezende, Marcos Caroli; Recueil des Travaux Chimiques des Pays-Bas; vol. 111; nb. 10; (1992); p. 448 - 450 View in Reaxys
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O O
O
O
alkali
HO
potassium
O
O
Rx-ID: 19674975 View in Reaxys 38/140 Yield
Conditions & References Reaction Steps: 2 2: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 2 min With dimethylsulfide, ozone Linderman, Russell J.; Chen, Kangyi; Tetrahedron Letters; vol. 33; nb. 45; (1992); p. 6767 - 6770 View in Reaxys
O
O Cl
(+-)-2-cyclohexa-1,4-dienyl-1-methyl-ethylamine O
O
O HO
potassium O
Rx-ID: 19717229 View in Reaxys 39/140 Yield
Conditions & References Reaction Steps: 2 1: 1) NaOH / 1) H2O, 2) 40 min 2: 1) NaH / 1) DMF, 2) rt, 2 h With sodium hydroxide, sodium hydride Cassels, Bruce K.; Radetski, Claudemir; Rezende, Marcos Caroli; Recueil des Travaux Chimiques des Pays-Bas; vol. 111; nb. 10; (1992); p. 448 - 450 View in Reaxys Reaction Steps: 2 1: 1) NaOH / 1) H2O, 2) 40 min 2: 1) C3H7SH, NaH / 1) DMF, 2) rt, 2 h With sodium hydroxide, sodium hydride Cassels, Bruce K.; Radetski, Claudemir; Rezende, Marcos Caroli; Recueil des Travaux Chimiques des Pays-Bas; vol. 111; nb. 10; (1992); p. 448 - 450 View in Reaxys O
N
O
O
O
O
HO O
O
O
Rx-ID: 1749294 View in Reaxys 40/140 Yield 62 %
Conditions & References With nickel(II) sulphate, ammonium hydroxide, sodium hydroxide, dipotassium peroxodisulfate in water, Time= 6h, Ambient temperature Yamazaki, Shigakazu; Yamazaki, Yasuyuki; Chemistry Letters; nb. 4; (1990); p. 571 - 574 View in Reaxys
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O O
OH
O HO
O
O O
O
O
Rx-ID: 2617041 View in Reaxys 41/140 Yield
Conditions & References With potassium hydroxide in methanol, Time= 8h, Heating, study of the alkaline degradation, Product distribution Gandhidasan, Rathinasamy; Neelakantan, Sthanusubramania; Raman, Pathai Venkateswara; Devaraj, Savithri; Phytochemistry (Elsevier); vol. 26; nb. 1; (1987); p. 281 - 284 View in Reaxys O
O N+
O S
O
I–
N+
HO
I–
HS
O
O
Rx-ID: 3175228 View in Reaxys 42/140 Yield
Conditions & References With cholinesterase, enzymatic hydrolysis Yamada; Marui; Hayashi; Takemura; Chemical and pharmaceutical bulletin; vol. 35; nb. 4; (1987); p. 1491 - 1496 View in Reaxys O I
O
O
O
O
O
HO O
O
O
Rx-ID: 2809537 View in Reaxys 43/140 Yield
Conditions & References With tetraethylammonium tosylate, triphenylphosphine, tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide, Pt anode/Pt cathode; electrolysis with 2.5 mA/cm2
13 %
Torii, Sigeru; Tanaka, Hideo; Hamatani, Takeshi; Morisaki, Kazuo; Jutand, Anny; et al.; Chemistry Letters; (1986); p. 169 - 172 View in Reaxys
O
O
O
O
O
O
OH
O O
HO
O
O
O O
O O
Rx-ID: 2609370 View in Reaxys 44/140 Yield 30 mg
Conditions & References With potassium hydroxide, dihydrogen peroxide in ethanol, water, Time= 0.25h, Heating, various reagent, solvent, temperature, time, Product distribution Rao, E. Venkata; Murthy, M. Sree Rama; Ward, Robert S.; Phytochemistry (Elsevier); vol. 23; nb. 7; (1984); p. 1493 - 1502
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View in Reaxys 30 mg
With potassium hydroxide, dihydrogen peroxide in ethanol, water, Time= 0.25h, Heating Rao, E. Venkata; Murthy, M. Sree Rama; Ward, Robert S.; Phytochemistry (Elsevier); vol. 23; nb. 7; (1984); p. 1493 - 1502 View in Reaxys
Si O
–O
O
O
N
O
S
HO
O O
O
N+
O O
N
Rx-ID: 2640418 View in Reaxys 45/140 Yield
Conditions & References With sodium hydroxide in water, Time= 3h, Ambient temperature Ohta, Shunsaku; Hayakawa, Satoshi; Okamoto, Masao; Tetrahedron Letters; vol. 25; nb. 49; (1984); p. 5681 - 5684 View in Reaxys
Si
O
N O
O HO N
O
O
N O
Rx-ID: 21459476 View in Reaxys 46/140 Yield
Conditions & References Reaction Steps: 2 1: 2 h / 70 °C 2: 74.7 percent / NaOH / H2O / 3 h / Ambient temperature With sodium hydroxide in water Ohta, Shunsaku; Hayakawa, Satoshi; Okamoto, Masao; Tetrahedron Letters; vol. 25; nb. 49; (1984); p. 5681 - 5684 View in Reaxys O
O N
O
O
HO N
O
O
Rx-ID: 21467947 View in Reaxys 47/140 Yield
Conditions & References Reaction Steps: 3 1: n-BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 2: 2 h / 70 °C 3: 74.7 percent / NaOH / H2O / 3 h / Ambient temperature With sodium hydroxide, n-butyllithium in tetrahydrofuran, hexane, water Ohta, Shunsaku; Hayakawa, Satoshi; Okamoto, Masao; Tetrahedron Letters; vol. 25; nb. 49; (1984); p. 5681 - 5684 View in Reaxys
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O
O O
O
O HO
HO OH
O O
O
O
Rx-ID: 1838600 View in Reaxys 48/140 Yield
Conditions & References With chromium(VI) oxide in acetic acid, Ambient temperature, Product distribution Anjaneyulu, A. S. R.; Ramaiah, P. Atchuta; Row, L. Ramachandra; Venkateswarlu, R.; Pelter, A.; Ward, R. S.; Tetrahedron; vol. 37; nb. 21; (1981); p. 3641 - 3652 View in Reaxys
O O
O
O
O
O
O
O
O
O
HO
O
O
O O
O O O
OH OH O O
Rx-ID: 3619230 View in Reaxys 49/140 Yield
Conditions & References With potassium hydroxide in ethanol, Time= 7h, Heating Nascimento, Maria Celia Do; Mors, Walter B.; Phytochemistry (Elsevier); vol. 20; (1981); p. 147 - 152 View in Reaxys
O O
O O
O
O O
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O
O
O O
O
O
O
HO
O
O
O O
OH
Rx-ID: 3620760 View in Reaxys 50/140 Yield
Conditions & References With potassium hydroxide in ethanol, Time= 2h, Heating Nascimento, Maria Celia Do; Mors, Walter B.; Phytochemistry (Elsevier); vol. 20; (1981); p. 147 - 152 View in Reaxys
HO
O
O
H
O HO O
O
O
H O OH
Rx-ID: 3880533 View in Reaxys 51/140 Yield
Conditions & References With chromium(VI) oxide in acetic acid, Ambient temperature, Product distribution Anjaneyulu, A. S. R.; Ramaiah, P. Atchuta; Row, L. Ramachandra; Venkateswarlu, R.; Pelter, A.; Ward, R. S.; Tetrahedron; vol. 37; nb. 21; (1981); p. 3641 - 3652 View in Reaxys HO O
O –O
Na + O
O O
O
O O O
HO HO
O O
O O OH
O
Rx-ID: 1748873 View in Reaxys 52/140 Yield 18.8 %, 18.0 %, 17.6 %
Conditions & References in dimethyl sulfoxide, T= 150 °C Kobayashi, Shigeru; Imakura, Yasuhiro; Horikawa, Ritsuko; Chemical & Pharmaceutical Bulletin; vol. 28; nb. 4; (1980); p. 1287 - 1293 View in Reaxys HO O
O O O O
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O
O O O
HO HO
O O
O O OH
O
Rx-ID: 1749280 View in Reaxys 53/140 Yield
Conditions & References
18.8 %, 18 %, 17.6 %
With sodium methylate in dimethyl sulfoxide, T= 150 °C Kobayashi, Shigeru; Imakura, Yasuhiro; Horikawa, Ritsuko; Chemical & Pharmaceutical Bulletin; vol. 28; nb. 4; (1980); p. 1287 - 1293 View in Reaxys
18.8 %, 18.0 %, 17.6 %
With sodium methylate in dimethyl sulfoxide, T= 150 °C Kobayashi, Shigeru; Imakura, Yasuhiro; Horikawa, Ritsuko; Chemical & Pharmaceutical Bulletin; vol. 28; nb. 4; (1980); p. 1287 - 1293 View in Reaxys Rx-ID: 1844419 View in Reaxys 54/140
Yield
Conditions & References
250 mg, 60 mg, 40 mg
With sulfuric acid in acetic acid, Heating Row, Ramachandra L.; Ventkateswarlu, Reveru; Tetrahedron Letters; vol. 21; (1980); p. 2919 - 2922 View in Reaxys
O OH
O
O
O
O
O
O
HO
O
O
O
O
O
O
O
Rx-ID: 3620298 View in Reaxys 55/140 Yield
Conditions & References With potassium permanganate, Product distribution Ghosal, Shibnath; Banerjee, Shanta; Jaiswal, Dinesh K.; Phytochemistry (Elsevier); vol. 19; (1980); p. 332 - 334 View in Reaxys O Br
O
O HO Li
O
O
O
Rx-ID: 115036 View in Reaxys 56/140 Yield
Conditions & References T= -35 °C , Behandeln des Reaktionsgemisches mit festem Kohlendioxid Gensler; Stouffer; Journal of Organic Chemistry; vol. 23; (1958); p. 908 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
23/46
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O Br
O
O HO O
O
Rx-ID: 115037 View in Reaxys 57/140 Yield
Conditions & References With n-butyllithium, diethyl ether, T= -35 °C , Behandeln des Reaktionsgemisches mit festem Kohlendioxid Gensler; Stouffer; Journal of Organic Chemistry; vol. 23; (1958); p. 908 View in Reaxys O O
O HO O
O
Rx-ID: 22375776 View in Reaxys 58/140 Yield
Conditions & References Reaction Steps: 2 1: chloroform; N-bromo-succinimide 2: butyl lithium; diethyl ether / -35 °C / Behandeln des Reaktionsgemisches mit festem Kohlendioxid With N-Bromosuccinimide, n-butyllithium, diethyl ether, chloroform Gensler; Stouffer; Journal of Organic Chemistry; vol. 23; (1958); p. 908 View in Reaxys
O O
O
O N
O HO
O
O
O
O
O
O
Rx-ID: 408221 View in Reaxys 59/140 Yield
Conditions & References With water, nitric acid, vanadia Dolce; Garofano; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1185,1196 View in Reaxys
O O
O
O N
O HO
O
O
O
O
O
O
Rx-ID: 424254 View in Reaxys 60/140 Yield
Conditions & References With water, nitric acid, vanadia Dolce; Garofano; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1185,1196
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View in Reaxys
O O
O O
O HO O
O
O
O
N
O
O
Rx-ID: 497826 View in Reaxys 61/140 Yield
Conditions & References With water, nitric acid, vanadia Dolce; Garofano; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1185,1196 View in Reaxys O
O
O
O
O
O HO
O
O
O
O
O
O
O
O
Rx-ID: 591638 View in Reaxys 62/140 Yield
Conditions & References With sodium amide, toluene Garofano; Oliverio; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 896,904 View in Reaxys
O O
O O
O HO O
O
O
N
O
O
O
Rx-ID: 675873 View in Reaxys 63/140 Yield
Conditions & References With water, nitric acid, vanadia Dolce; Garofano; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1185,1196 View in Reaxys O O O HO O O
Rx-ID: 809053 View in Reaxys 64/140
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Yield
Conditions & References With potassium permanganate Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056 View in Reaxys O O
O HO O
O
Rx-ID: 809058 View in Reaxys 65/140 Yield
Conditions & References With potassium permanganate Naves; Ardizio; Bulletin de la Societe Chimique de France; (1957); p. 1053,1056 View in Reaxys
O O
O N
OH
vanadium (V)-oxide
O
O
O
O
O N
O HO
O
O
O
O
Rx-ID: 5456500 View in Reaxys 66/140 Yield
Conditions & References Dolce; Garofano; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1185,1196 View in Reaxys
O
O Na + H
O
O
–N
O
H
O
O
O O
O HO O
O
O O
Rx-ID: 5527994 View in Reaxys 67/140 Yield
Conditions & References Garofano; Oliverio; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 896,904 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O O
O HO O
O
Rx-ID: 22377126 View in Reaxys 68/140 Yield
Conditions & References Reaction Steps: 2 1: acetic acid; sulfuric acid 2: water; vanadium(V)-oxide; nitric acid With sulfuric acid, water, nitric acid, vanadia, acetic acid Dolce; Garofano; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1185,1196 View in Reaxys Reaction Steps: 2 1: acetic acid; concentrated sulfuric acid 2: water; vanadium(V)-oxide; nitric acid With sulfuric acid, water, nitric acid, vanadia, acetic acid Dolce; Garofano; Annali di Chimica (Rome, Italy); vol. 47; (1957); p. 1185,1196 View in Reaxys
O
H 2N
aqueous potassium hypobromite solution
O
HN
O O HN
O
HN
N
O
O HO
O O
O
O
O
NH
O
O
Rx-ID: 5501409 View in Reaxys 69/140 Yield
Conditions & References Rodionow; Kiselewa; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1953); p. 513,514; ; (1954); p. 9968 View in Reaxys O
H HO
O
O
O
N
O
N
O
HO
O
O
O
O
Rx-ID: 810577 View in Reaxys 70/140 Yield
Conditions & References La Parola; Gazzetta Chimica Italiana; vol. 73; (1943); p. 94,97 View in Reaxys
4-bromo-3-nitro-5-<3-hydroxy-propyl>-2-<3,4-methylenedioxyphenyl>-2,3-dihydro-benzofuranol-(2)
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
27/46
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Br
O HO
O
OH
HO HO
O O
Rx-ID: 8138848 View in Reaxys 71/140 Yield
Conditions & References With potassium hydroxide Kawai et al.; Chemische Berichte; vol. 73; (1940); p. 1328; Nippon Kagaku Kaishi; vol. 62; (1941); p. 112 View in Reaxys H
O O
O
N
HO
OH
O N
HO
N O
O
O
O
Rx-ID: 810558 View in Reaxys 72/140 Yield
Conditions & References T= 100 °C Jordan; Hauser; Journal of the American Chemical Society; vol. 58; (1936); p. 1304 View in Reaxys H
O
O
N O
O
O
O
HO
N
NH
O
O
Rx-ID: 831966 View in Reaxys 73/140 Yield
Conditions & References T= 100 °C Hauser; Jordan; Journal of the American Chemical Society; vol. 58; (1936); p. 1772,1775 View in Reaxys H N
O
O N
N
O
O
O
H
O
O
HO
O N
HO
O
O
Rx-ID: 831967 View in Reaxys 74/140 Yield
Conditions & References T= 100 °C Hauser; Jordan; Journal of the American Chemical Society; vol. 58; (1936); p. 1772,1775 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
O O
O HO
(-)-hinokinin
O
O
O H 2N
H O
OH
Rx-ID: 5682177 View in Reaxys 75/140 Yield
Conditions & References With sodium amide, benzene Keimatsu; Ishiguro; Yakugaku Zasshi; vol. 56; (1936); p. 103,105, 113; Chem. Zentralbl.; vol. 107; nb. II; (1936); p. 1743 View in Reaxys H
O N O
O
O
ethanolic NaOH-solution NH
O
N O
O
O
N
HO OH
O
O
O
Rx-ID: 5707795 View in Reaxys 76/140 Yield
Conditions & References T= 0 °C Hauser; Jordan; Journal of the American Chemical Society; vol. 58; (1936); p. 1772,1775 View in Reaxys H O
O
O N
N O
O
O
H
O
O
HO
O N
HO
O
O
Rx-ID: 821999 View in Reaxys 77/140 Yield
Conditions & References T= 100 °C Hauser; Jordan; O'Connor; Journal of the American Chemical Society; vol. 57; (1935); p. 2456 View in Reaxys
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O
O
O
O
HO
HO
aqueous palladium(II)-chloride-solution
O
O
Rx-ID: 5446389 View in Reaxys 78/140 Yield
Conditions & References Gulland; Macrae; Journal of the Chemical Society; (1932); p. 2231,2235 View in Reaxys
HO
O N O O
O
OH
O
O
O
O
O HO
potassium permanganate
O
Rx-ID: 5446397 View in Reaxys 79/140 Yield
Conditions & References Spaeth; Schmidt; Monatshefte fuer Chemie; vol. 53/54; (1929); p. 469 View in Reaxys O
OH
O
O O
OH
N
N
O
O
N
O
O
N O
O
O HO
methanolic KOH-solution
O
Rx-ID: 6801742 View in Reaxys 80/140 Yield
Conditions & References Kochen des Reaktionsprodukts mit Natronlauge Holter; Bretschneider; Monatshefte fuer Chemie; vol. 53/54; (1929); p. 978 View in Reaxys O
OH
O
O O
OH
N
N
O
O
N
O
O
N O
O
O
methanolic KOH-solution
H N
O
H N
O
HO
O
O
O
Rx-ID: 6995421 View in Reaxys 81/140 Yield
Conditions & References anschl. mit wss.NaOH
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Holter; Bretschneider; Monatshefte fuer Chemie; vol. 53/54; (1929); p. 978 View in Reaxys O
H N
O N
O O
alkaline potassium permanganate solution
O
N
HO
O O
Rx-ID: 5446387 View in Reaxys 82/140 Yield
Conditions & References Quilico; Freri; Gazzetta Chimica Italiana; vol. 58; (1928); p. 385,388,390; Gazzetta Chimica Italiana; vol. 59; (1929); p. 606 View in Reaxys
O
O
O
O
O
O
chromium trioxide O
O
O
O
O HO
O
Rx-ID: 5446390 View in Reaxys 83/140 Yield
Conditions & References (+)-sesamin Bertram; van der Steur; Waterman; Biochemische Zeitschrift; vol. 197; (1928); p. 5 View in Reaxys OH
O S O
permanganate
O
O
O O
O
O
O
OH
HO O
O
Rx-ID: 5678433 View in Reaxys 84/140 Yield
Conditions & References Chattaway; Morris; Journal of the Chemical Society; (1927); p. 2017 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
O H N
N
O
O
O
N
O
HO
O O
O
O
O
Rx-ID: 831963 View in Reaxys 85/140 Yield
Conditions & References O-anilinoformyl-β-piperonal oxime Brady; McHugh; Journal of the Chemical Society; vol. 127; (1925); p. 2421 View in Reaxys
O
O
O
O
O O
O
O
N Cl
N
O
HO
H
HO
N
O N
O
O O
O
N
O N
N
O
O
O
Rx-ID: 5628332 View in Reaxys 86/140 Yield
Conditions & References β-piperonal oxime O-picryl ether Brady; Klein; Journal of the Chemical Society; vol. 127; (1925); p. 846 View in Reaxys
O O
O
O
N
O
O
O
N
O
HO
O O N
O
O O N O
Rx-ID: 838101 View in Reaxys 87/140 Yield
Conditions & References Brady; Truszkowski; Journal of the Chemical Society; vol. 125; (1924); p. 1093 View in Reaxys
O
O
NH
N O O
O N
O
O O
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2018-06-02 11:30:57
O
O
O
HO
O
NH
NH NH 2
Rx-ID: 833265 View in Reaxys 88/140 Yield
Conditions & References O-β-naphthylaminoformyl-β-piperonal oxime Brady; Ridge; Journal of the Chemical Society; vol. 123; (1923); p. 2173 View in Reaxys
O
O O
OH
O O
permanganate
O
HO
O O
O O
Rx-ID: 5446393 View in Reaxys 89/140 Yield
Conditions & References Mameli; Gazzetta Chimica Italiana; vol. 51 II; (1921); p. 354; Gazzetta Chimica Italiana; vol. 65; (1935); p. 886 View in Reaxys
O O
O
O HO
β-piperonal oxime O
N
O
N
O
O O
3.5-bis-<3.4-methylenedioxy-phenyl>-1.2.4-oxadiazole
3.5-bis-<3.4-methylenedioxy-phenyl>-1.2.4-oxadiazole-4-oxide Rx-ID: 5543283 View in Reaxys 90/140
Yield
Conditions & References Robin; Annales de Chimie (Cachan, France); vol. <9> 16; (1921); p. 120 View in Reaxys O
O
β-oxy-β-<3.4-methylenedioxy-phenyl>-β-butylene
HO
O
Rx-ID: 5446382 View in Reaxys 91/140 Yield
Conditions & References With permanganate(VII) ion Korjukin; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 43; (1911); p. 208; Chem. Zentralbl.; vol. 82; nb. I; (1911); p. 1852 View in Reaxys
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O
OH
O
O
HO
permanganate O
O
Rx-ID: 5446392 View in Reaxys 92/140 Yield
Conditions & References Korjukin; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 43; (1911); p. 208; Chem. Zentralbl.; vol. 82; nb. I; (1911); p. 1852 View in Reaxys O
O
O N H
permanganate O
O O
O
O
HO O
O
Rx-ID: 5446403 View in Reaxys 93/140 Yield
Conditions & References Thoms; Thuemen; Chemische Berichte; vol. 44; (1911); p. 3727 View in Reaxys
O O
alcoholic KOH-solution O
O O O
HO HO O
O
Rx-ID: 5446404 View in Reaxys 94/140 Yield
Conditions & References Pauly; Buttlar; Justus Liebigs Annalen der Chemie; vol. 383; (1911); p. 236 Anm. View in Reaxys Fittig; Mielck; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 52,54; Justus Liebigs Annalen der Chemie; vol. 172; (1874); p. 140,152 View in Reaxys HO
O
O
potassium permanganate O
OH
O
natrium carbonate containing solution
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O
HO
O
O
O
O
O
OH
HO O
O
O
OH
Rx-ID: 5678506 View in Reaxys 95/140 Yield
Conditions & References β-methyl-β-<3.4-methylenedioxy-phenyl>-β.β-pentadiene-β.β-dicarboxylic acid Stobbe; Justus Liebigs Annalen der Chemie; vol. 380; (1911); p. 31 View in Reaxys
O
potassium permanganate
N O
alkali
O
O
O HO
O
Rx-ID: 5446398 View in Reaxys 96/140 Yield
Conditions & References Angeli; Alessandri; Pegna; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 19 I; (1910); p. 654 View in Reaxys
O
O
potassium permanganate O
O O
O
O
HO
O
O
HO
Rx-ID: 5466659 View in Reaxys 97/140 Yield
Conditions & References Luff; Perkin; Robinson; Journal of the Chemical Society; vol. 97; (1910); p. 1139 View in Reaxys O
O
3.4-methylenedioxy-phenyl-glyoxylic acid nitrile
HO
O
Rx-ID: 5446383 View in Reaxys 98/140 Yield
Conditions & References With water Ewins; Journal of the Chemical Society; vol. 95; (1909); p. 1485 View in Reaxys
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O
O
O
H
O
H
HO
O
N O
O
Rx-ID: 5446384 View in Reaxys 99/140 Yield
Conditions & References Ewins; Journal of the Chemical Society; vol. 95; (1909); p. 1485 View in Reaxys
O O
aqueous KOH-solution O
O O O
HO HO O
O
Rx-ID: 5446406 View in Reaxys 100/140 Yield
Conditions & References Barger; Journal of the Chemical Society; vol. 93; (1908); p. 565; Chemische Berichte; vol. 42; (1909); p. 763 View in Reaxys
O
O
O
O
OH
permanganate
O
O
HO
O
O HO
diluted KOH-solution
O
O
OH
Rx-ID: 5589102 View in Reaxys 101/140 Yield
Conditions & References Pomeranz; Monatshefte fuer Chemie; vol. 8; (1887); p. 468 View in Reaxys Mameli; Gazzetta Chimica Italiana; vol. 37 II; (1907); p. 505 View in Reaxys
NH OH
N O
alkali
air
O
O O
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O H
O
H
O
N
HO
H
HO
O
Rx-ID: 5690804 View in Reaxys 102/140 Yield
Conditions & References Nowosielski; Chem. Zentralbl.; vol. 78; nb. I; (1907); p. 1798 View in Reaxys O O
O
O
O
HO
N O
O
O
Rx-ID: 123110 View in Reaxys 103/140 Yield
Conditions & References im Sonnenlicht Ciamician; Silber; Chemische Berichte; vol. 38; (1905); p. 3821; Gazzetta Chimica Italiana; vol. 36 II; (1906); p. 201 View in Reaxys Ciamician; Silber; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5>14II; (1905); p. 377; Chemische Berichte; vol. 38; (1905); p. 1181,3815 View in Reaxys O
OH H N
O
O
HO
potassium permanganate O
O
Rx-ID: 5446395 View in Reaxys 104/140 Yield
Conditions & References Barger; Jowett; Journal of the Chemical Society; vol. 87; (1905); p. 973 View in Reaxys
O O
alcoholic NaOH-solution O
O O O
HO HO O
O
Rx-ID: 5446405 View in Reaxys 105/140 Yield
Conditions & References Decker; Koch; Chemische Berichte; vol. 38; (1905); p. 1741 View in Reaxys O NH
2
O
OH NH 2 HO
S OO
HO
alkaline solution
O
O
ammonia O
Rx-ID: 8426019 View in Reaxys 106/140
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Yield
Conditions & References Davis; Journal of the Chemical Society; vol. 87; (1905); p. 1834 View in Reaxys O
O
O
O
O HO O
O
O
HO
O
Rx-ID: 165327 View in Reaxys 107/140 Yield
Conditions & References With sodium hypobromide Wallach; Mueller,H.; Justus Liebigs Annalen der Chemie; vol. 332; (1904); p. 331 View in Reaxys
O
sodium hypobromite O
O
O
O O
O HO
O
HO
O
Rx-ID: 5466653 View in Reaxys 108/140 Yield
Conditions & References Wallach; Mueller,H.; Justus Liebigs Annalen der Chemie; vol. 332; (1904); p. 331 View in Reaxys O
O
O
O
O HO O
O
HO
O
Rx-ID: 132177 View in Reaxys 109/140 Yield
Conditions & References With potassium permanganate, acetic acid Miller; Archiv der Pharmazie (Weinheim, Germany); vol. 240; (1902); p. 377 View in Reaxys Tiemann; Chemische Berichte; vol. 24; (1891); p. 2881 View in Reaxys
O
O O
potassium permanganate O
O
O O
O
O
HO
O
O
12.13-dioxy-3.4-methylene-dioxy-1-propyl-benzene
HO
Rx-ID: 5466661 View in Reaxys 110/140
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Yield
Conditions & References Miller; Archiv der Pharmazie (Weinheim, Germany); vol. 240; (1902); p. 377 View in Reaxys Wagner; Bouschmakin; Chemische Berichte; vol. 24; (1891); p. 3489 View in Reaxys Tiemann; Chemische Berichte; vol. 24; (1891); p. 2881 View in Reaxys Poleck; Chemische Berichte; vol. 19; (1886); p. 1094; Chemische Berichte; vol. 22; (1889); p. 2862 View in Reaxys Eijkman; Recueil des Travaux Chimiques des Pays-Bas; vol. 4; (1885); p. 39 View in Reaxys Wagner; Chemische Berichte; vol. 21; (1888); p. 3351 View in Reaxys O
O
O
O
alkaline potassium permanganate
HO
O
O
Rx-ID: 5446388 View in Reaxys 111/140 Yield
Conditions & References in der Hitze Bougault; Bulletin de la Societe Chimique de France; vol. <3> 25; (1901); p. 857; Annales de Chimie (Cachan, France); vol. <7> 25; (1902); p. 552 View in Reaxys
O
O
O
O O
O
HO
alcoholic KOH-solution
O
O
O
Rx-ID: 5446385 View in Reaxys 112/140 Yield
Conditions & References Biltz; Wienands; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 14 View in Reaxys
O
O
O
O O
O
O
potassium hydroxide
HO
O O
Rx-ID: 5446394 View in Reaxys 113/140 Yield
Conditions & References beim Schmelzen Biltz; Wienands; Justus Liebigs Annalen der Chemie; vol. 308; (1899); p. 14 View in Reaxys
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O
O
O–
O
Na +
O
O
O HO
2-aceto-naphthol-(1) O
Rx-ID: 5540195 View in Reaxys 114/140 Yield
Conditions & References v. Kostanecki; Chemische Berichte; vol. 31; (1898); p. 707 View in Reaxys O O
O
O
HO
alkaline potassium hypobromite O
O
Rx-ID: 5446386 View in Reaxys 115/140 Yield
Conditions & References van Linge; Recueil des Travaux Chimiques des Pays-Bas; vol. 16; (1897); p. 45 View in Reaxys O
O HO
pseudocubebin
O
Rx-ID: 5446400 View in Reaxys 116/140 Yield
Conditions & References With potassium permanganate Peinemann; Archiv der Pharmazie (Weinheim, Germany); vol. 234; (1896); p. 258 View in Reaxys O
O HO
Cl
O
O
HO
HO
N H
H O
NH 2
O
O
O
Rx-ID: 5690483 View in Reaxys 117/140 Yield
Conditions & References Heffter; Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie; vol. 35; (1895); p. 350 View in Reaxys
O O
O
KOH-solution
O
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
O
O
HO
O
paracotoinic acid
O
O
Rx-ID: 5742192 View in Reaxys 118/140 Yield
Conditions & References Jobst; Hesse; Justus Liebigs Annalen der Chemie; vol. 199; (1879); p. 20,21 View in Reaxys Ciamician; Silber; Chemische Berichte; vol. 26; (1893); p. 2341,2345; Chemische Berichte; vol. 27; (1894); p. 424,847 View in Reaxys Ciamician; Silber; Gazzetta Chimica Italiana; vol. 23 II; (1893); p. 195,202; Gazzetta Chimica Italiana; vol. 24 I; (1894); p. 431,541 View in Reaxys Hesse; Justus Liebigs Annalen der Chemie; vol. 282; (1894); p. 199; Chemische Berichte; vol. 28; (1895); p. 2508 View in Reaxys
O O
potassium hydroxide
O
O
O
OH O
OH
O
O
O
O
HO
OH H
O
O
HO
Rx-ID: 5446407 View in Reaxys 119/140 Yield
Conditions & References beim Schmelzen Jobst; Hesse; Justus Liebigs Annalen der Chemie; vol. 199; (1879); p. 20,21 View in Reaxys Ciamician; Silber; Gazzetta Chimica Italiana; vol. 23 II; (1893); p. 195,202; Gazzetta Chimica Italiana; vol. 24 I; (1894); p. 431,541 View in Reaxys O
O
O
HO
O
O
O
Rx-ID: 136160 View in Reaxys 120/140 Yield
Conditions & References With alkaline potassium permanganate Ciamician; Silber; Gazzetta Chimica Italiana; vol. 22 I; (1892); p. 473; Chemische Berichte; vol. 25; (1892); p. 1127 View in Reaxys O
O
protocotoin-methyl ether
HO
O
Rx-ID: 5446399 View in Reaxys 121/140
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Yield
Conditions & References With chloroform, bromine Ciamician; Silber; Chemische Berichte; vol. 25; (1892); p. 1123 View in Reaxys
O O
alkaline potassium permanganate O
O
O
HO
O
O
HO
O
O
O
Rx-ID: 5469043 View in Reaxys 122/140 Yield
Conditions & References Ciamician; Silber; Gazzetta Chimica Italiana; vol. 22 I; (1892); p. 473; Chemische Berichte; vol. 25; (1892); p. 1127 View in Reaxys
O
Cl
O
Cl
O
bromine in excess Cl O
O
O
O
O HO
tribromophloroglucinoltrimethyl ether O
Rx-ID: 5747415 View in Reaxys 123/140 Yield
Conditions & References Ciamician; Silber; Gazzetta Chimica Italiana; vol. 22 I; (1892); p. 470; Chemische Berichte; vol. 25; (1892); p. 1125 View in Reaxys O
O
O
O
O
O
HO O
O
HO
O
Rx-ID: 247930 View in Reaxys 124/140 Yield
Conditions & References bei der Oxydation Tiemann; Chemische Berichte; vol. 24; (1891); p. 2881 View in Reaxys O O
O
O O
HO
HO
O
Rx-ID: 247944 View in Reaxys 125/140
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Yield
Conditions & References With potassium permanganate, acetic acid Tiemann; Chemische Berichte; vol. 24; (1891); p. 2881 View in Reaxys
O HO
potassium permanganate
OH
O
O O
O
O
O
O
HO
O
O
HO
O
Rx-ID: 5466660 View in Reaxys 126/140 Yield
Conditions & References Tiemann; Chemische Berichte; vol. 24; (1891); p. 2881 View in Reaxys
O
aqueous potassium permanganate O
O
O
HO
O
O
HO
3.4-methylenedioxy-mandelic acid O
O
O
Rx-ID: 5543174 View in Reaxys 127/140 Yield
Conditions & References Garelli; Gazzetta Chimica Italiana; vol. 21 II; (1891); p. 175 View in Reaxys O
O O
HO
O
O
HO O
O
O
O
Rx-ID: 809022 View in Reaxys 128/140 Yield
Conditions & References With potassium permanganate, water Ciamician; Silber; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <4> 6 I; (1890); p. 443; Gazzetta Chimica Italiana; vol. 20; (1890); p. 571 View in Reaxys Ciamician; Silber; Chemische Berichte; vol. 23; (1890); p. 1165 View in Reaxys O
O
O
O
HO
HO
O
O
Rx-ID: 812756 View in Reaxys 129/140
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Yield
Conditions & References With potassium permanganate Fittig; Mielck; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 52,54; Justus Liebigs Annalen der Chemie; vol. 172; (1874); p. 140,152 View in Reaxys Doebner; Chemische Berichte; vol. 23; (1890); p. 2378; Chemische Berichte; vol. 24; (1891); p. 1746 View in Reaxys
O
aqueous potassium permanganate O
O
O
O
HO
O
HO
O
O
O
Rx-ID: 5469044 View in Reaxys 130/140 Yield
Conditions & References Ciamician; Silber; Gazzetta Chimica Italiana; vol. 20; (1890); p. 571; Chemische Berichte; vol. 23; (1890); p. 1160 View in Reaxys O
O HO
potassium permanganate
alkali
O
HO
O
O
HO
O
HO
O
O
O
H
HO H
O
OH
O
O O
OH
OH
Rx-ID: 5589115 View in Reaxys 131/140 Yield
Conditions & References T= 3 °C Fittig; Mielck; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 52,54; Justus Liebigs Annalen der Chemie; vol. 172; (1874); p. 140,152 View in Reaxys Doebner; Chemische Berichte; vol. 23; (1890); p. 2378; Chemische Berichte; vol. 24; (1891); p. 1746 View in Reaxys
O
O
O
HO
O HO
O
O
O
Rx-ID: 828525 View in Reaxys 132/140 Yield
Conditions & References With potassium permanganate Pomeranz; Monatshefte fuer Chemie; vol. 10; (1889); p. 786,787; Monatshefte fuer Chemie; vol. 9; (1888); p. 864 View in Reaxys
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O
O
O
alkaline potassium-permanganate solution
HO
O
O O
O
O
HO O
O
Rx-ID: 5446401 View in Reaxys 133/140 Yield
Conditions & References T= 50 °C , β-methoxy-β-<3.4-methylenedioxy-cinnamal>-crotonic acid Pomeranz; Monatshefte fuer Chemie; vol. 9; (1888); p. 864; Monatshefte fuer Chemie; vol. 10; (1889); p. 786 View in Reaxys O
O HO
cubebin
O
Rx-ID: 5446391 View in Reaxys 134/140 Yield
Conditions & References With potassium permanganate Pomeranz; Monatshefte fuer Chemie; vol. 8; (1887); p. 468 View in Reaxys O
O HO
alkaline potassium permanganate solution O
O
HO
O
O HO
β.β-dioxy-β-<3.4-methylenedioxy-phenyl>-n-valeric acid O
O
OH
Rx-ID: 8470406 View in Reaxys 135/140 Yield
Conditions & References Regel; Chemische Berichte; vol. 20; (1887); p. 415 View in Reaxys O O
O
O
O
HO O
O
O
Rx-ID: 132174 View in Reaxys 136/140 Yield
Conditions & References With potassium permanganate Poleck; Chemische Berichte; vol. 19; (1886); p. 1094; Chemische Berichte; vol. 22; (1889); p. 2862 View in Reaxys
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O O
O HO O
O
Rx-ID: 132176 View in Reaxys 137/140 Yield
Conditions & References With potassium permanganate Poleck; Chemische Berichte; vol. 19; (1886); p. 1094; Chemische Berichte; vol. 22; (1889); p. 2862 View in Reaxys Eijkman; Recueil des Travaux Chimiques des Pays-Bas; vol. 4; (1885); p. 39 View in Reaxys O
OH O
I
O
I
HO
OH O
HO
Rx-ID: 144807 View in Reaxys 138/140 Yield
Conditions & References With potassium hydroxide, T= 140 °C , im Rohr; Behandeln des Reaktionsprodukts mit alkoh. Kalilauge Fittig; Remsen; Justus Liebigs Annalen der Chemie; vol. 168; (1873); p. 94 View in Reaxys O O
O
H
O
H
potassium permanganate
O
HO
O
O
Rx-ID: 5446396 View in Reaxys 139/140 Yield
Conditions & References Fittig; Mielck; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 52,54; Justus Liebigs Annalen der Chemie; vol. 172; (1874); p. 140,152 View in Reaxys
O
O
O
permanganate
HO
O
O O
O
O
HO O
O
Rx-ID: 5446402 View in Reaxys 140/140 Yield
Conditions & References Goebel; Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 32; p. 117 View in Reaxys
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