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23 reactions in Reaxys
2018-04-22 11h:40m:56s (UTC)
OH HO
1. Query
O O
Search as: As drawn
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I
OH
HO
HO O
O
O O
Rx-ID: 310185 View in Reaxys 1/23 Yield 91 %
Conditions & References With sodium hydroxide, copper(II) sulfate in water, Reflux Altemoeller, Martina; Gehring, Timo; Cudaj, Judith; Podlech, Joachim; Goesmann, Helmut; Feldmann, Claus; Rothenberger, Alexander; European Journal of Organic Chemistry; nb. 13; (2009); p. 2130 - 2140 View in Reaxys
64 %
With copper(II) sulfate, sodium hydroxide in water, Time= 16h, Reflux Varró, Gábor; Hegedűs, László; Simon, András; Kádas, István; Tetrahedron Letters; vol. 57; nb. 14; (2016); p. 1544 - 1546 View in Reaxys With sodium hydroxide, copper Smith; Journal of the Chemical Society; (1958); p. 3740 View in Reaxys With potassium fluoride in dichloromethane, N,N-dimethyl-formamide Taniguchi, Eiji; Imamura, Keiichi; Ishabashi, Fumito; Matsui, Toshio; Nishio, Akira; Agricultural and Biological Chemistry; vol. 53; nb. 3; (1989); p. 631 - 644 View in Reaxys
2.53 g
With sodium hydroxide, copper(II) sulfate in water, Time= 4h, Heating, Substitution Hyotylainen; Chemosphere; vol. 28; nb. 9; (1994); p. 1641 - 1656 View in Reaxys With sodium hydroxide, copper(II) sulfate, Time= 6h, T= 125 °C Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio; Organic and biomolecular chemistry; vol. 1; nb. 14; (2003); p. 2474 - 2485 View in Reaxys
35.26 g
With copper(ll) sulfate pentahydrate, sodium hydroxide in water, Reflux Varró, Gábor; Hegedus, László; Simon, András; Balogh, Attila; Grün, Alajos; Leveles, Ibolya; Vértessy, Beáta G.; Kádas, István; Journal of Natural Products; vol. 80; nb. 6; (2017); p. 1909 - 1917 View in Reaxys With copper(ll) sulfate pentahydrate, sodium hydroxide in water, Time= 20h, Reflux Varró, Gábor; Mattyasovszky, Lenke; Grün, Alajos; Simon, András; Hegedüs, László; Kádas, István; Synthesis (Germany); vol. 50; nb. 3; (2018); p. 625 - 643; Art.No: SS-2017-T0559-OP View in Reaxys OH
HO
O
HO O
O O
Rx-ID: 22063505 View in Reaxys 2/23 Yield
Conditions & References Reaction Steps: 2 1: glacial acetic acid / 25 °C / durch Bromierung 2: NaOH-solution; copper / 200 - 210 °C With sodium hydroxide, copper, acetic acid Shriner; McCutchan; Journal of the American Chemical Society; vol. 51; (1929); p. 2194
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View in Reaxys 1.ii : EXAMPLE 1 (ii) 0.200 mole of vanillin (impurity originating from the previous stages for the preparation of 4,5-dihydroxy-3-methoxybenzaldehyde). Patent; Rhone-Poulenc Chimie; US5003091; (1991); (A) English View in Reaxys 4 : EXAMPLE 4 EXAMPLE 4 Vanillin (20 mmole) was iodinated and converted to 5-hydroxyvanillin as set forth in Examples 1-3. Patent; International Telephone and Telegraph Corporation; US4465864; (1984); (A) English View in Reaxys Reaction Steps: 2 1.1: bromine / acetic acid / 1 h / 18 °C 2.1: sodium hydroxide; copper / water / 24 h / Reflux 2.2: 1 h / Reflux With bromine, copper, sodium hydroxide in water, acetic acid Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882 View in Reaxys Reaction Steps: 2 1: iodine; potassium iodide; potassium carbonate / water / 3 h / 20 °C 2: sodium hydroxide; copper(II) sulfate / water / 16 h / Reflux With iodine, potassium carbonate, copper(II) sulfate, potassium iodide, sodium hydroxide in water Varró, Gábor; Hegedűs, László; Simon, András; Kádas, István; Tetrahedron Letters; vol. 57; nb. 14; (2016); p. 1544 - 1546 View in Reaxys Reaction Steps: 2 1: sodium hydrogencarbonate; potassium iodide; iodine / water / 3.5 h / 20 °C 2: copper(ll) sulfate pentahydrate; sodium hydroxide / water / Reflux With copper(ll) sulfate pentahydrate, iodine, sodium hydrogencarbonate, potassium iodide, sodium hydroxide in water Varró, Gábor; Hegedus, László; Simon, András; Balogh, Attila; Grün, Alajos; Leveles, Ibolya; Vértessy, Beáta G.; Kádas, István; Journal of Natural Products; vol. 80; nb. 6; (2017); p. 1909 - 1917 View in Reaxys Reaction Steps: 2 1: sodium hydrogencarbonate; potassium iodide; iodine / water / 3 h / 20 °C 2: copper(ll) sulfate pentahydrate; sodium hydroxide / water / 20 h / Reflux With copper(ll) sulfate pentahydrate, iodine, sodium hydrogencarbonate, potassium iodide, sodium hydroxide in water Varró, Gábor; Mattyasovszky, Lenke; Grün, Alajos; Simon, András; Hegedüs, László; Kádas, István; Synthesis (Germany); vol. 50; nb. 3; (2018); p. 625 - 643; Art.No: SS-2017-T0559-OP View in Reaxys Br
OH
HO
HO O
O
O O
Rx-ID: 310176 View in Reaxys 3/23 Yield 97 %
Conditions & References With copper, sodium hydroxide in water, Time= 24h, Heating Pettit, George R.; Thornhill, Andrew; Melody, Noeleen; Knight, John C.; Journal of Natural Products; vol. 72; nb. 3; (2009); p. 380 - 388
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View in Reaxys 93 %
Stage 1: With copper, sodium hydroxide in water, Time= 24h, Reflux Stage 2: With disodium hydrogenphosphate in water, Time= 1h, Reflux Cervi, Aymeric; Aillard, Paul; Hazeri, Nourallah; Petit, Laurent; Chai, Christina L. L.; Willis, Anthony C.; Banwell, Martin G.; Journal of Organic Chemistry; vol. 78; nb. 19; (2013); p. 9876 - 9882 View in Reaxys
90 %
2.2.2. Synthesis of 3,4-dihydroxy-5-methoxybenzaldehyde (compound 2) To a suspension of 5-bromovanillin (1, 9.2 g, 38.4 mmol) and NaOH (15.4 g, 384.8 mmol) in degassed water (400 mL), was added Cu powder (123 mg, 1.92 mmol) at room temperature (RT). The reaction mixture was refluxed for 60 h and then cooled down to RT. Na2HPO4 (273 mg, 1.92 mmol) was added to the reaction mixture and refluxed for 1 h. The reaction mixture was subsequently filtered and the filtered solid was rinsed with water. The filtrate collected was acidified with 6 N HCl until acidic. The resulting mixture was evaporated at 60 C under reduced pressure (30 mmHg) until a thick slurry remained. The slurry was dissolved in ethyl acetate (500 mL), then dried with MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (5percent MeOH/DCM) to give compound 2 (6 g, yield of 90percent) as a light brown solid [18] with mp 131-133 C. 1H NMR (400 MHz, CDCl3): d 9.79 (s, 1H),7.14 (d, J 1.7 Hz, 1H), 7.08 (d, J 1.7 Hz, 1H), 3.97 (s, 3H). 13C NMR(101 MHz, DMSO) d 191.3,148.5,145.9,141.1,127.4,110.9,105.0, 56.0.ESI-MS: m/z 167.3 for C8H9O4 ([M - H]-, calculated m/z 167.0). Stage 1: With copper, sodium hydroxide in water, Time= 60h, Reflux Stage 2: With disodium hydrogenphosphate in water, Time= 1h, Reflux Zhang, Jieyu; Cheah, Yong Shung; Santhanakrishnan, Sridhar; Neoh, Koon Gee; Chai, Christina L.L.; Polymer (United Kingdom); vol. 116; (2017); p. 5 - 15 View in Reaxys
80 %
With copper, sodium hydroxide in water, Time= 24h, Reflux Kuo, Ping-Chung; Chen, Yi-Hsien; Leu, Yann-Lii; Huang, Chieh-Hung; Liao, Yu-Ren; Lee, E.-Jian; Yang, Mei-Lin; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 4; (2012); p. 557 - 561 View in Reaxys
64 %
With copper, sodium hydroxide in water, Time= 27h, Reflux Tsyganov, Dmitry V.; Konyushkin, Leonid D.; Karmanova, Irina B.; Firgang, Sergei I.; Strelenko, Yuri A.; Semenova, Marina N.; Kiselyov, Alex S.; Semenov, Victor V.; Journal of Natural Products; vol. 76; nb. 8; (2013); p. 1485 - 1491 View in Reaxys
62 %
5.2.6. 3,4-Dihydroxy-5-methoxybenzaldehyde (14) 5-Bromovanilin 13 (20 g, 91 mmol), NaOH (24.5 g, 610 mol) and copper powder (0.1 g, 1.6 mmol) were slurred into water (300 mL). The reaction mixture was heated at reflux for 24-27 h. Disodium hydrogen phosphate (0.45 g, 3.2 mmol) was added at the last half hour of reflux. The reaction was then cooled at 50 °C, filtered to remove a precipitate of cupric hydrogen phosphate and acidified with HCl (46 g). The reaction mixture was extracted with EtOAc and separated by silica gel column chromatography using n-hexane:EtOAc (6:4) as eluents to yield 14 (9.5 g, 62percent) as a colorless solid, m.p. 132-134 °C; IR (neat) νmax 3278, 1674, 1593, 1523, 1462, 1334, 1207, 1141, 1091, 1002, 840, 717 cm-1; 1HNMR (300 MHz, DMSO-d6) ν 9.68 (1H, s, CHO), 9.50 (1H, s, OH), 9.44 (1H, s, OH), 7.01 (2H, s), 3.81 (3H, s, OMe); 13CNMR (75 MHz, DMSO-d6) ν 191.3, 148.5, 146.0, 141.1, 127.4, 110.9, 105.0, 56.0; EIMS m/z (rel. int.): 168 [M]+ (100), 167 (79), 125 (18), 97 (16); HREIMS calcd for C8H8O4 [M]+ 168.0423, found 168.0423. Stage 1: With copper, sodium hydroxide in water, Reflux Stage 2: With disodium hydrogenphosphate in water, Reflux Stage 3: With hydrogenchloride in water Huang, Guan-Jhong; Bhaskar Reddy, M. Vijaya; Kuo, Ping-Chung; Huang, Chieh-Hung; Shih, Hung-Cheng; Lee, E.Jian; Yang, Mei-Lin; Leu, Yann-Lii; Wu, Tian-Shung; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 371 378 View in Reaxys
60 %
With sodium hydroxide, copper in water, Time= 25.5h, T= 101 °C Ellis, James E.; Lenger, Steven R.; Synthetic Communications; vol. 28; nb. 9; (1998); p. 1517 - 1524 View in Reaxys
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60 %
With water, copper, sodium hydroxide, Time= 18h, Reflux Luo, Wen; Li, Yan-Ping; Tan, Jia-Heng; Gu, Lian-Quan; Huang, Zhi-Shu; Journal of Enzyme Inhibition and Medicinal Chemistry; vol. 26; nb. 5; (2011); p. 706 - 711 View in Reaxys
48.1 %
With potassium hydroxide, copper, Time= 1h, T= 210 °C Lam; Iiyama; Stone; Phytochemistry; vol. 41; nb. 6; (1996); p. 1507 - 1510 View in Reaxys With sodium hydroxide, copper, T= 200 - 210 °C Shriner; McCutchan; Journal of the American Chemical Society; vol. 51; (1929); p. 2194 View in Reaxys Bradley; Robinson; Schwarzenbach; Journal of the Chemical Society; (1930); p. 796,811 View in Reaxys With copper, sodium hydroxide in water, Reflux Luo, Wen; Li, Yan-Ping; He, Yan; Huang, Shi-Liang; Tan, Jia-Heng; Ou, Tian-Miao; Li, Ding; Gu, Lian-Quan; Huang, Zhi-Shu; Bioorganic and Medicinal Chemistry; vol. 19; nb. 2; (2011); p. 763 - 770 View in Reaxys OH
HO
OH OH
HO
O
HO
O O O
O OH
Rx-ID: 44285543 View in Reaxys 4/23 Yield
Conditions & References With NADH, Enzymatic reaction Rahmanpour, Rahman; King, Lloyd D.W.; Bugg, Timothy D.H.; Biochemical and Biophysical Research Communications; vol. 482; nb. 1; (2017); p. 57 - 61 View in Reaxys HO
HO
O
OH
O
2H
2H 2
H
2H
O
2
2H
H
O
Rx-ID: 11261463 View in Reaxys 5/23 Yield
Conditions & References Stage 1: With sodium hydroxide, iodine, potassium iodide in water, Time= 8h, T= 20 °C Stage 2: With sodium hydroxide, copper(II) sulfate, Time= 4h, T= 145 °C , Further stages. Sakakibara, Norikazu; Nakatsubo, Tomoyuki; Suzuki, Shiro; Shibata, Daisuke; Shimada, Mikio; Umezawa, Toshiaki; Organic and Biomolecular Chemistry; vol. 5; nb. 5; (2007); p. 802 - 815 View in Reaxys Reaction Steps: 2 1: I2; KI; aq. NaOH / 2 h / 20 °C 2: aq. NaOH; CuSO4 / 6 h / 125 °C With sodium hydroxide, iodine, copper(II) sulfate, potassium iodide Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio; Organic and biomolecular chemistry; vol. 1; nb. 14; (2003); p. 2474 - 2485 View in Reaxys
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OH
HO HO
O –O
HO
Na +
O O
Br
Rx-ID: 9390104 View in Reaxys 6/23 Yield
Conditions & References
71 %
With copper dichloride in N,N-dimethyl-formamide, Time= 2h, Heating Russell, Wendy R.; Burkitt, Mark J.; Scobbie, Lorraine; Chesson, Andrew; Bioorganic Chemistry; vol. 31; nb. 3; (2003); p. 206 - 215 View in Reaxys HO
I
HO
O
OH
O
2H
2H 2H
2H
2H
O
2H
O
Rx-ID: 9422407 View in Reaxys 7/23 Yield
Conditions & References With sodium hydroxide, copper(II) sulfate, Time= 6h, T= 125 °C Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio; Organic and biomolecular chemistry; vol. 1; nb. 14; (2003); p. 2474 - 2485 View in Reaxys OH
HO
HO
iron (II)-chloride
O
O
O O
Rx-ID: 14041417 View in Reaxys 8/23 Yield
Conditions & References Reaction Steps: 2 1: I2; KI; aq. NaOH / 2 h / 20 °C 2: aq. NaOH; CuSO4 / 6 h / 125 °C With sodium hydroxide, iodine, copper(II) sulfate, potassium iodide Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio; Organic and biomolecular chemistry; vol. 1; nb. 14; (2003); p. 2474 - 2485 View in Reaxys 2
H 2H
O
HO
OH
2H
O
O 2
H 2
2H
H
O
O
Rx-ID: 14054188 View in Reaxys 9/23 Yield
Conditions & References Reaction Steps: 3 1: aq. HCl / acetic acid / 1 h / Heating 2: I2; KI; aq. NaOH / 2 h / 20 °C 3: aq. NaOH; CuSO4 / 6 h / 125 °C With hydrogenchloride, sodium hydroxide, iodine, copper(II) sulfate, potassium iodide in acetic acid Sakakibara, Norikazu; Suzuki, Shiro; Umezawa, Toshiaki; Shimada, Mikio; Organic and biomolecular chemistry; vol. 1; nb. 14; (2003); p. 2474 - 2485 View in Reaxys
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OH HO
HO
O
O O
HO
Rx-ID: 14091903 View in Reaxys 10/23 Yield
Conditions & References Reaction Steps: 2 1: 67 percent / bromine; acetic acid 2: 71 percent / copper(II) chloride / dimethylformamide / 2 h / Heating With bromine, acetic acid, copper dichloride in N,N-dimethyl-formamide Russell, Wendy R.; Burkitt, Mark J.; Scobbie, Lorraine; Chesson, Andrew; Bioorganic Chemistry; vol. 31; nb. 3; (2003); p. 206 - 215 View in Reaxys OH
O HO O
O O HO
O
Rx-ID: 8708149 View in Reaxys 11/23 Yield 63 %
Conditions & References With pyridine, aluminium trichloride in dichloromethane, Time= 72h, T= 20 °C , Demethylation Zouhiri, Fatima; Mouscadet, Jean-Francois; Mekouar, Khalid; Desmaele, Didier; Savoure, Delphine; Leh, Herve; Subra, Frederic; Le Bret, Marc; Auclair, Christian; D'Angelo, Jean; Journal of Medicinal Chemistry; vol. 43; nb. 8; (2000); p. 1533 - 1540 View in Reaxys OH
HO
O
HO O
hydrazinecarboxylic acid ethyl ester hydrochloride
O O
Rx-ID: 17638595 View in Reaxys 12/23 Yield
Conditions & References Reaction Steps: 2 1: 88 percent / acetic acid, bromine / 2 h / Ambient temperature 2: 48.1 percent / copper, 10percent KOH / 1 h / 210 °C With potassium hydroxide, bromine, copper, acetic acid Lam; Iiyama; Stone; Phytochemistry; vol. 41; nb. 6; (1996); p. 1507 - 1510 View in Reaxys OH
HO
O
HO O
5.7-dimethoxy-4-methyl-flavylium chloride
O O
Rx-ID: 16524259 View in Reaxys 13/23 Yield
Conditions & References Reaction Steps: 2 1: 16.2 g / iodomonochloride; aq. HCl 2: 2.53 g / CuSO4*5H2O; NaOH / H2O / 4 h / Heating With hydrogenchloride, sodium hydroxide, Iodine monochloride, copper(II) sulfate in water, 1: Iodination / 2: Substitution Hyotylainen; Chemosphere; vol. 28; nb. 9; (1994); p. 1641 - 1656 View in Reaxys
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OH
O
HO
O
O Br
OH
O
OH
Rx-ID: 2161450 View in Reaxys 14/23 Yield
Conditions & References
69 %
With silver, sodium hydrogencarbonate, sodium iodide, zinc in 1,2-dimethoxyethane, dimethyl sulfoxide, Time= 0.666667h, T= 60 °C Chung, Chi Kong; Ho, Mei Sing; Lun, Kue Sun; Wong, Man On; Wong, Henry N. C.; Tam, Shang Wai; Synthetic Communications; vol. 18; nb. 5; (1988); p. 507 - 510 View in Reaxys
OH
O O
O
O
HO
O
HO
O
O
O
O
O
O
HO
O
O HO
HO
O
Rx-ID: 2432624 View in Reaxys 15/23 Yield
Conditions & References With aluminium(III) iodide, tetra-(n-butyl)ammonium iodide in cyclohexane, Time= 6h, other reaction time, other molar ratios of educt/AlI3 and educt/catalyst, Product distribution Andersson, Sven; Synthesis; nb. 4; (1985); p. 437 - 439 View in Reaxys OH HO O O
Rx-ID: 7189499 View in Reaxys 16/23 Yield
Conditions & References Patent; Hoffmann-LaRoche and Co.; DE2248337; (1972); ; vol. 80; nb. 14741 View in Reaxys Asakawa et al.; Phytochemistry (Elsevier); vol. 15; (1976); p. 1057 View in Reaxys Lange; Journal of Organic Chemistry; vol. 27; (1962); p. 2037 View in Reaxys Banerjee et al.; Canadian Journal of Chemistry; vol. 40; (1962); p. 2175 View in Reaxys OH HO
N O
O
HO O
aqueous .K2S2O8
O O
Rx-ID: 5807822 View in Reaxys 17/23 Yield
Conditions & References und Erwaermen des Reaktionsgemisches mit wss.HCl Baker; Brown; Journal of the Chemical Society; (1948); p. 2303,2306 View in Reaxys
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O
O O
OH
O
O
HO
O O
O O O Cl
Rx-ID: 517921 View in Reaxys 18/23 Yield
Conditions & References With Pd-BaSO4, toluene, T= 110 °C , Hydrogenation.Behandeln einer aethanol.Loesung des Reaktionsprodukts mit wss.NaOH unter Wasserstoff Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2>133; (1932); p. 120,123,124 View in Reaxys
HO
OH
OH
HO
HO O
O O
O
Rx-ID: 22003156 View in Reaxys 19/23 Yield
Conditions & References Reaction Steps: 3 1: aq. NaOH solution 2: chloroform; phosphorus (V)-chloride 3: toluene; palladium/barium sulfate / 110 °C / Hydrogenation.Behandeln einer aethanol.Loesung des Reaktionsprodukts mit wss.NaOH unter Wasserstoff With sodium hydroxide, Pd-BaSO4, chloroform, phosphorus pentachloride, toluene Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2>133; (1932); p. 120,123,124 View in Reaxys O
O O
OH
O
O
HO
O O
O O O HO
Rx-ID: 22018564 View in Reaxys 20/23 Yield
Conditions & References Reaction Steps: 2 1: chloroform; phosphorus (V)-chloride 2: toluene; palladium/barium sulfate / 110 °C / Hydrogenation.Behandeln einer aethanol.Loesung des Reaktionsprodukts mit wss.NaOH unter Wasserstoff With Pd-BaSO4, chloroform, phosphorus pentachloride, toluene Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2>133; (1932); p. 120,123,124 View in Reaxys OH
O
HO O
O O HO
O
Rx-ID: 292270 View in Reaxys 21/23 Yield
Conditions & References With sodium hydroxide, dihydrogen peroxide Patent; Hoffmann-La Roche; DE350650; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 566 View in Reaxys
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OH
O
HO N
H
O
O O
H
O
O O
HO
O
Rx-ID: 7189500 View in Reaxys 22/23 Yield
Conditions & References Patent; Hoffmann-La Roche; DE530650; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 566 View in Reaxys OH HO
5-nitro-veratrum-aldehyde
O O
Rx-ID: 7189501 View in Reaxys 23/23 Yield
Conditions & References With hydrogenchloride, tin, Diazotieren in schwefelsaurer Loesung und nachfolgendes Erhitzen im Kohlendioxydstrom auf dem Wasserbad Spaeth; Roeder; Monatshefte fuer Chemie; vol. 43; (1922); p. 107 View in Reaxys
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