2,4,5-trimethoxybenzaldehyde [CAS 4460-86-0; InChIKey IAJBQAYHSQIQRE-UHFFFAOYSA-N; Reaxys, All Preps

Query Query

Results

Date

37 reactions in Reaxys

2016-02-22 06h:52m:50s (EST)

O O

1. Query O

O

Search as: As drawn

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OH O

O

O O

O

O

O

Rx-ID: 8751306 View in Reaxys 1/37 Yield 97%

Conditions & References 2.3. Typical procedure for oxidation of alcohols General procedure: The copper salt and the ligand (each 0.025 mmol) were added to CH3CN (1 mL) in an Ar atmosphere and stirred for 30min. Then 4-OH-TEMPO (0.025 mmol) and substrate (0.5mmol) were added successively, and the mixture was stirred at room temperature. The reaction progress was checked using thin-layer chromatography. The reaction conversion and yield were obtained from GC measurements using nitrobenzene or nonane as an internal standard, or by column chromatography.

With copper(l) iodide, prostab 5198, bpmen in acetonitrile, Time= 2h, T= 20 °C , Inert atmosphere Zhang, Shufang; Miao, Chengxia; Xu, Daqian; Sun, Wei; Xia, Chungu; Chinese Journal of Catalysis; vol. 35; nb.

11; (2014); p. 1864 - 1873 View in Reaxys

96 %

With tetrapropylammonium perruthennate, 4-methylmorpholine N-oxide in dichloromethane, Time= 1.5h, T= 0 °C , Molecular sieve, Inert atmosphere Takaya, Yoshiaki; Hotta, Rie; Fujiwara, Kenshu; Otani, Risa; Uchiyama, Yurika; Sakakibara, Mizuki; Fukuda, Eri; Niwa, Masatake; Inouye, Kei; Oohata, Akiko A.; Organic Letters; vol. 16; nb. 14; (2014); p. 3660 - 3663 View in Reaxys With cerium (IV) sulfate, AzBTS2- in sulfuric acid, acetonitrile, T= 25 °C , Kinetics, Thermodynamic data, Further Variations: Reagents Branchi, Barbara; Galli, Carlo; Gentili, Patrizia; Organic and Biomolecular Chemistry; vol. 3; nb. 14; (2005); p. 2604 - 2614 View in Reaxys With disodium octaborate, dipotassium peroxodisulfate, tert-butyl alcohol, T= 25 °C , pH= 10, Radiolysis Baciocchi, Enrico; Bietti, Massimo; Gerini, Maria Francesca; Manduchi, Laura; Salamone, Michela; Steenken, Steen; Chemistry - A European Journal; vol. 7; nb. 7; (2001); p. 1408 - 1416 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, 1,10-phenanthroline, oxygen, copper(II) sulfate in sodium hydroxide, Time= 5h, T= 100 °C , p= 7500.75Torr , pH= 13.5, Product distribution Figiel, Pawel J.; Leskelae, Markku; Repo, Timo; Advanced Synthesis and Catalysis; vol. 349; nb. 7; (2007); p. 1173 - 1179 View in Reaxys Reaction Steps: 2 1: NaH / tetrahydrofuran 2: aq. K2S2O8; 2-methyl-2-propanol; disodium tetraborate decahydrate / 25 °C / pH 10 / Radiolysis With disodium octaborate, dipotassium peroxodisulfate, sodium hydride, tert-butyl alcohol in tetrahydrofuran Baciocchi, Enrico; Bietti, Massimo; Gerini, Maria Francesca; Manduchi, Laura; Salamone, Michela; Steenken, Steen; Chemistry - A European Journal; vol. 7; nb. 7; (2001); p. 1408 - 1416 View in Reaxys With CuSO4‵5H2O, 2,2,6,6-tetramethylpiperidine-N-oxyl, (4-fluorophenyl)(1H-pyrrol-2-ylmethylene)amine, dihydrogen peroxide, potassium carbonate in water, Time= 1h, T= 60 °C Ahmad, Jahir Uddin; Raeisaenen, Minna T.; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol.

411-412; (2012); p. 180 - 187 View in Reaxys

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O

O

O O

O

O

O

Rx-ID: 334603 View in Reaxys 2/37 Yield

Conditions & References

83 %

With sodium periodate, osmium(VIII) oxide, N-benzyl-N,N,N-triethylammonium chloride in tetrahydrofuran, water, T= 100 °C , Microwave irradiation Kumar, Rakesh; Sharma, Prabha; Shard, Amit; Tewary, Dhananjay Kumar; Nadda, Gireesh; Sinha, Arun Kumar; Medicinal Chemistry Research; vol. 21; nb. 6; (2012); p. 922 - 931 View in Reaxys With chromium(VI) oxide Fabinyi; Szeki; Chemische Berichte; vol. 39; (1906); p. 1217 View in Reaxys Beckstroem; Archiv der Pharmazie (Weinheim, Germany); vol. 242; (1904); p. 99 View in Reaxys Rizza; Butlerow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 19; (1887); p. 3; Chemische Berichte; vol. 20; (1887); p. Ref., 223 View in Reaxys With potassium permanganate Fabinyi; Szeki; Chemische Berichte; vol. 39; (1906); p. 1217 View in Reaxys Beckstroem; Archiv der Pharmazie (Weinheim, Germany); vol. 242; (1904); p. 99 View in Reaxys Rizza; Butlerow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 19; (1887); p. 3; Chemische Berichte; vol. 20; (1887); p. Ref., 223 View in Reaxys With chloroform, und Zersetzung des entstandenen Ozonids mit Eis und Calciumcarbonat van Alphen; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 198; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 174 View in Reaxys With acetic acid ester, und Zersetzung des entstandenen Ozonids mit Eis und Calciumcarbonat van Alphen; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 198; Recueil des Travaux Chimiques des Pays-Bas; vol. 47; (1928); p. 174 View in Reaxys With hydrogenchloride, EtO-NO Fabinyi; Szeki; Chemische Berichte; vol. 50; (1917); p. 1338 View in Reaxys With diethyl ether, nitrobenzene Alessandri; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 24 I; (1915); p. 63; Gazzetta Chimica Italiana; vol. 51 II; (1921); p. 135 View in Reaxys

O

O O

Z O O

O

O

Rx-ID: 9519907 View in Reaxys 3/37

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Yield

Conditions & References

83 %

With sodium periodate, osmium(VIII) oxide, N-benzyl-N,N,N-triethylammonium chloride in tetrahydrofuran, water, T= 100 °C , Microwave irradiation Kumar, Rakesh; Mohanakrishnan, Dinesh; Sharma, Abhishek; Kaushik, Naveen Kumar; Kalia, Kalpana; Sinha, Arun Kumar; Sahal, Dinkar; European Journal of Medicinal Chemistry; vol. 45; nb. 11; (2010); p. 5292 - 5301 View in Reaxys

82 %

With sodium periodate, osmium(VIII) oxide, N-benzyl-N,N,N-triethylammonium chloride in tetrahydrofuran, water, Time= 0.0138889h, microwave irradiation Sinha, Arun K.; Joshi, Bhupendra P.; Acharya, Ruchi; Chemistry Letters; vol. 32; nb. 8; (2003); p. 780 - 781 View in Reaxys With dipyridinium dichromate, acetic acid in 1,4-dioxane, Time= 0.333333h, Heating, Microwave irradiation Sharma, Abhishek; Sharma, Naina; Shard, Amit; Kumar, Rakesh; Mohanakrishnan, Dinesh; Saima; Sinha, Arun K.; Sahal, Dinkar; Organic and Biomolecular Chemistry; vol. 9; nb. 14; (2011); p. 5211 - 5219 View in Reaxys Synthesis of 2,4,5-trimethoxy benzaldehyde from β-asarone β-Asarone ((E)-2,4,5-trimethoxy-1-propenylbenzene) was converted into 2,4,5-trimethoxy benzaldehyde by using KMnO4/NaHCO3 With potassium permanganate, sodium hydrogencarbonate, T= 20 °C Shenvi, Suvarna; Kumar, Krishna; Hatti, Kaushik S.; Rijesh; Diwakar, Latha; Reddy, G. Chandrasekara; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 435 - 442 View in Reaxys

O O

O

O

N

O

O

O

O

Rx-ID: 3342995 View in Reaxys 4/37 Yield 81 %

Conditions & References With trichlorophosphate, Time= 1h, T= 20 °C , Vilsmeier reaction Lin, Yung-Lung; Wu, Chung-Shieh; Lin, Shean-Woei; Huang, Jian-Lin; Sun, Yang-Sheng; Yang, Ding-Yah; Bioorganic and Medicinal Chemistry; vol. 10; nb. 3; (2002); p. 685 - 690 View in Reaxys With trichlorophosphate Birch,A.J. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1975); p. 2492 - 2501 View in Reaxys Jackson,A.H.; Martin,J.A.; Journal of the Chemical Society [Section] C: Organic; (1966); p. 2222 - 2229 View in Reaxys

9.80 g

With trichlorophosphate, 0 deg C, then 80 deg C, 1 h Ishii; Ishikawa; Deushi; et al.; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3024 - 3038 View in Reaxys

O

O

THF-H2O

Z O

asaronaldehyde (2,4,5-trimethoxybenzalde‐ hyde)

O

O

O

O

Rx-ID: 24136631 View in Reaxys 5/37

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Yield

Conditions & References

2.39 g (82%)

I.a : Reaction: STR1 (a) Preparation of asaronaldehyde (2,4,5-trimethoxybenzaldehyde) from β-asarone (by microwave irradiation method): A mixture of β-asarone (3.1 g, 0.015 mmol), catalytic amount of OsO4 (0.04 to 0.002 g), NaIO4 (11.75 g, 0.055 mmol), benzyltriethyl ammonium chloride (catalytic amount) and THF-H2O (8-10 mL, 4:1) were taken in a 100 ml Erlenmeyer flask fitted with a loose funnel at the top.

The flask was shaken well and placed inside a microwave oven operating at medium power level and irradiated for 2-12 minutes in parts.

After completion of the reaction (monitored by TLC), the contents of the flask were poured into chloroform and passed through a bed of Celite and further washed with chloroform.

The filtrate and washings were combined and the chloroform layer were washed with sodium thiosulphate to destroy the excess periodate.

The chloroform layers were then combined and washed with saturated sodium chloride (3*15 m), dried over anhydrous sodium sulphate and filtered.

The solvent was removed to afford a crude solid product which was recrytallised with water to afford 2.39 g (82percent) of asaronaldehyde as a feathery white needles, Rf (0.34 in 28percent ethylacetate in hexane); mp 114° C. (lit. mp 114° C.); IR (film) vmax 1662 (carbonyl group), 1620, 1518, 1481, 1419, 1361, 1300, 1278, 1222, 1199, 1138, 1025, 865 cm-1; 1H NMR δ 10.32 (1H, s, CHO), 7.33 (1H, s, 6H), 6.50 (1H, s, 3H), 3.98 (3H, s, 2-OCH3),3.93 ((3H, s, 4-OCH3), 3.88 (3H, s, 5-OCH3); 13 C NMR δ 187.96 (CHO), 158.60 (C-2), 155.76 (C-4), 143.56 (C-5), 117.35 (C-1), 109.03 (C-6), 56.19 (2-OCH3, 4-OCH3 and 5-OCH3); EIMS m/z 196 [M]+(100), 181 (49),150 (32),125 (33), 110(23), 69 (37).

With sodium periodate, OsO4 Patent; Sinha, Arun Kumar; Joshi, Bhupendra Prasad; Dogra, Ruchi; US2002/153240; (2002); (A1) English View in Reaxys

O

O

O E O

O

O

O

Rx-ID: 9519908 View in Reaxys 6/37 Yield

Conditions & References

84 %

With sodium periodate, osmium(VIII) oxide, N-benzyl-N,N,N-triethylammonium chloride in tetrahydrofuran, water, microwave irradiation Sinha, Arun K.; Joshi, Bhupendra P.; Acharya, Ruchi; Chemistry Letters; vol. 32; nb. 8; (2003); p. 780 - 781 View in Reaxys

82 %

With sodium periodate, osmium(VIII) oxide, N-benzyl-N,N,N-triethylammonium chloride in tetrahydrofuran, water, Microwave irradiation Sharma, Upendra K.; Sood, Swati; Sharma, Nandini; Rahi, Praveen; Kumar, Rakesh; Sinha, Arun K.; Gulati, Arvind; Medicinal Chemistry Research; vol. 22; nb. 11; (2013); p. 5129 - 5140 View in Reaxys

O

O

O

O

O

O O O

O

O

N NH

O

O

O N

N N

Rx-ID: 33407546 View in Reaxys 7/37 Yield 66 %

Conditions & References With copper (II) acetate monohydrate in toluene, Time= 7h, T= 60 °C

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Guru, Murali Mohan; Punniyamurthy, Tharmalingam; Journal of Organic Chemistry; vol. 77; nb. 11; (2012); p. 5063 - 5073 View in Reaxys

O O O O N

O

O

O

O

O

O

Cl

O

O

O

O

O

O

O O

Rx-ID: 28202323 View in Reaxys 8/37 Yield

Conditions & References

56 %, 24 % With AlCl3, aluminium chloride in chlorobenzene, Time= 22h, T= 0 - 18 °C Kantlehner, Willi; Anders, Ernst; Mezger, Jochen; Stoyanov, Edmont V.; Kress, Ralf; Wermann, Kurt; Frey, Wolfgang; Goerls, Helmar; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 63; nb. 4; (2008); p. 395 - 406 View in Reaxys

O

O

O

O

O

O

O O

OH

Rx-ID: 38596432 View in Reaxys 9/37 Yield

Conditions & References Reaction Steps: 2 1: borane-THF / tetrahydrofuran / 1.5 h / 0 - 20 °C / |Inert atmosphere 2: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 1.5 h / 0 °C / |Molecular sieve; |Inert atmosphere With tetrapropylammonium perruthennate, borane-THF, 4-methylmorpholine N-oxide in tetrahydrofuran, dichloromethane Takaya, Yoshiaki; Hotta, Rie; Fujiwara, Kenshu; Otani, Risa; Uchiyama, Yurika; Sakakibara, Mizuki; Fukuda, Eri; Niwa, Masatake; Inouye, Kei; Oohata, Akiko A.; Organic Letters; vol. 16; nb. 14; (2014); p. 3660 - 3663 View in Reaxys

O

O

O

O O

O

O

O

Rx-ID: 8777998 View in Reaxys 10/37 Yield

Conditions & References With disodium octaborate, dipotassium peroxodisulfate, tert-butyl alcohol, T= 25 °C , pH= 10, Radiolysis Baciocchi, Enrico; Bietti, Massimo; Gerini, Maria Francesca; Manduchi, Laura; Salamone, Michela; Steenken, Steen; Chemistry - A European Journal; vol. 7; nb. 7; (2001); p. 1408 - 1416 View in Reaxys

O

O

O

O

O O O

O

O

O O

Rx-ID: 9691055 View in Reaxys 11/37

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Yield

Conditions & References

77 %

With ammonium acetate, Time= 0.0125h, microwave irradiation Mitra, Alok Kumar; Karchaudhuri, Nilay; De, Aparna; Journal of Chemical Research; nb. 3; (2004); p. 237 - 239 View in Reaxys

O

O

O O

O

O

O

Rx-ID: 2025038 View in Reaxys 12/37 Yield

Conditions & References With sodium dichromate in acetic acid, benzene, Time= 6h, Heating Kulkarni, Mandakini M.; Sohoni, Jayant S.; Rojatkar, Supada R.; Nagasampagi, Bhimsen A.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 25; (1986); p. 981 - 982 View in Reaxys

O O

O

O

N

O

O

O

Rx-ID: 194557 View in Reaxys 13/37 Yield

Conditions & References With hydrogenchloride, aluminium trichloride, benzene, T= 40 - 50 °C , Zersetzung des Reaktionsgemisches mit Eiswasser Gattermann; Eggers; Chemische Berichte; vol. 32; (1899); p. 290 View in Reaxys

O

O

O

OH O

HO

O

Rx-ID: 818713 View in Reaxys 14/37 Yield

Conditions & References With sodium hydroxide, dipotassium peroxodisulfate Ponniah; Seshadri; Proceedings - Indian Academy of Sciences, Section A; vol. 37; (1953); p. 544,548 View in Reaxys Reaction Steps: 3 1: Br2; NaClO3 2: CuCl 3: NaOH With sodium chlorate, sodium hydroxide, bromine, copper(l) chloride Chen, Lianqing; Yang, Chuluo; Li, Suyue; Qin, Jingui; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 68; nb. 2; (2007); p. 317 - 322 View in Reaxys

O O

calmus oil O

O

Rx-ID: 7186252 View in Reaxys 15/37

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Yield

Conditions & References With sodium hydrogensulfite, beim Stehen an der Luft Thoms; Beckstroem; Chemische Berichte; vol. 34; (1901); p. 1022; Chemische Berichte; vol. 35; (1902); p. 3188 View in Reaxys With water, sodium hydrogensulfite Thoms; Beckstroem; Chemische Berichte; vol. 35; (1902); p. 3195,3196, 3197 View in Reaxys

O

O

O N

O

O

O

O

O

N O

O

O

O

O O

O

O O

O

O

O Oerythro erythro O O

O

O

O

O N

O

O

O O threo threo O O

O

O

O N

O

O

N

N

O

O N O

O

N O

O

O

Rx-ID: 9130716 View in Reaxys 16/37 Yield

Conditions & References in acetonitrile, T= 25 °C Zhao; Li; Journal of Chemical Research - Part S; nb. 10; (2001); p. 430 - 432 View in Reaxys

O

HO O

H OH O

O

O

Br

Rx-ID: 11329364 View in Reaxys 17/37 Yield

Conditions & References Reaction Steps: 2 1: CuCl 2: NaOH With sodium hydroxide, copper(l) chloride Chen, Lianqing; Yang, Chuluo; Li, Suyue; Qin, Jingui; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 68; nb. 2; (2007); p. 317 - 322 View in Reaxys

O O

HO

OH

O

O

Rx-ID: 11341617 View in Reaxys 18/37 Yield

Conditions & References Reaction Steps: 4 1: POCl3 2: Br2; NaClO3 3: CuCl

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4: NaOH With sodium chlorate, sodium hydroxide, bromine, copper(l) chloride, trichlorophosphate, 1: Vilsmeier reaction Chen, Lianqing; Yang, Chuluo; Li, Suyue; Qin, Jingui; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 68; nb. 2; (2007); p. 317 - 322 View in Reaxys

O

O

O

O O

O

O O

O

O

O

OH

Rx-ID: 334604 View in Reaxys 19/37 Yield

Conditions & References With potassium permanganate, water Poleck; Chemische Berichte; vol. 17; (1884); p. 1416 View in Reaxys Rizza; Butlerow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 19; (1887); p. 3; Chemische Berichte; vol. 20; (1887); p. Ref., 223 View in Reaxys Rizza; Butlerow; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1887); p. 1336 View in Reaxys

O HO

OH

O

O

O S

O

O

O

O

O

O

Rx-ID: 11187805 View in Reaxys 20/37 Yield

Conditions & References With sodium hydroxide Chen, Lianqing; Yang, Chuluo; Li, Suyue; Qin, Jingui; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 68; nb. 2; (2007); p. 317 - 322 View in Reaxys

O O

O O

OH

O

O

Rx-ID: 22242109 View in Reaxys 21/37 Yield

Conditions & References Reaction Steps: 2 1: HCl; diethyl ether / Erwaermen des Reaktionsprodukts mit Wasser 2: K2CO3; acetone With hydrogenchloride, diethyl ether, potassium carbonate, acetone Head; Robertson; Journal of the Chemical Society; (1930); p. 2434,2437 View in Reaxys

O O

O O

NH 2

O

O

Rx-ID: 22274903 View in Reaxys 22/37

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Yield

Conditions & References Reaction Steps: 3 1: aqueous H2SO4 / Diazotization 2: HCl; diethyl ether / Erwaermen des Reaktionsprodukts mit Wasser 3: K2CO3; acetone With hydrogenchloride, diethyl ether, sulfuric acid, potassium carbonate, acetone Head; Robertson; Journal of the Chemical Society; (1930); p. 2434,2437 View in Reaxys

O HO

OH

O

I O

O

O

O

Rx-ID: 840148 View in Reaxys 23/37 Yield

Conditions & References With potassium carbonate, acetone Head; Robertson; Journal of the Chemical Society; (1931); p. 1241,1244 View in Reaxys

O

O

O

O

I

O O

O

OH

Rx-ID: 842172 View in Reaxys 24/37 Yield

Conditions & References With potassium carbonate, acetone Head; Robertson; Journal of the Chemical Society; (1930); p. 2434,2437 View in Reaxys

O

HO O

O

I

O

O

O

OH

Rx-ID: 842295 View in Reaxys 25/37 Yield

Conditions & References With potassium carbonate, acetone Head; Robertson; Journal of the Chemical Society; (1930); p. 2434,2437 View in Reaxys

O

O

Z

O

E

O

O

O

E

O

O

O

O

O

O

O

O

O

O

O

O

O

O

Rx-ID: 2021144 View in Reaxys 26/37 Yield 1.18 g, 0.28 g, 0.19 g, 0.26 g

Conditions & References Time= 720h, Irradiation, Further byproducts given Saxena, D. B.; Mukerjee, S. K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 24; (1985); p. 683 - 684 View in Reaxys

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0.28 g, 0.26 g, 0.19 g, 1.18 g

Time= 720h, Irradiation, Further byproducts given

1.18 g, 0.26 g, 0.19 g, 0.28 g

Time= 720h, Irradiation, Further byproducts given

1.18 g, 0.28 g, 0.26 g, 0.19 g

Time= 720h, Irradiation, Further byproducts given

Saxena, D. B.; Mukerjee, S. K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 24; (1985); p. 683 - 684 View in Reaxys

Saxena, D. B.; Mukerjee, S. K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 24; (1985); p. 683 - 684 View in Reaxys

Saxena, D. B.; Mukerjee, S. K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 24; (1985); p. 683 - 684 View in Reaxys

O

O

O

O

O

Z

E

O

O

HO

O

O O

O

O

O

O

Rx-ID: 1580073 View in Reaxys 27/37 Yield

Conditions & References Time= 4h, Irradiation Gracza; Archiv der Pharmazie; vol. 315; nb. 6; (1982); p. 571 - 574 View in Reaxys

O

O

O

O

O

Z

O

E

O

Z

O

O

O

O

O

O

O

O

O

O O

O

O

Rx-ID: 2021142 View in Reaxys 28/37 Yield

Conditions & References

1.18 g, 0.28 g, 0.26 g, 46 mg

Time= 720h, Irradiation, Further byproducts given Saxena, D. B.; Mukerjee, S. K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 24; (1985); p. 683 - 684 View in Reaxys

O

O

O

O O

KMnO4

O

O O

O

O

O

OH

Rx-ID: 7368212 View in Reaxys 29/37 Yield

Conditions & References Thoms; Beckstroem; Chemische Berichte; vol. 35; (1902); p. 3195,3196, 3197 View in Reaxys Beckstroem; Archiv der Pharmazie (Weinheim, Germany); vol. 242; (1904); p. 99 View in Reaxys Poleck; Chemische Berichte; vol. 17; (1884); p. 1416 View in Reaxys Rizza; Butlerow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 19; (1887); p. 3; Chemische Berichte; vol. 20; (1887); p. Ref., 223

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View in Reaxys

O

O

O

Cl (v6)

O

O

5-methoxy-2-propyl-benzoquinone(1.4)

CS2

Cr O Cl

O

O

O

Rx-ID: 7918504 View in Reaxys 30/37 Yield

Conditions & References Beckstroem; Archiv der Pharmazie (Weinheim, Germany); vol. 242; (1904); p. 99 View in Reaxys

O

O

O

O

O

O

O O

HO

O

O

O

O

OH

Rx-ID: 379733 View in Reaxys 31/37 Yield

Conditions & References Moore; Journal of the Chemical Society; vol. 99; (1911); p. 1044 View in Reaxys

O

O O

O

OH

K2cr2O7

O

O

O

O

Rx-ID: 7186253 View in Reaxys 32/37 Yield

Conditions & References Rizza; Butlerow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 19; (1887); p. 3; Chemische Berichte; vol. 20; (1887); p. Ref., 223 View in Reaxys

O

O O O

ethanolic KOH

O

O

N

O

O

O

O

N

O

O N

O

O

O

Rx-ID: 7982787 View in Reaxys 33/37 Yield

Conditions & References Erhitzen Bruckner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 138; (1933); p. 268,270 View in Reaxys

O

O O

OH HO

S OO

O

Z N O

HO O

NH 2

O

O

Rx-ID: 8236452 View in Reaxys 34/37 Yield

Conditions & References Alessandri; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 24 I; (1915); p. 63; Gazzetta Chimica Italiana; vol. 51 II; (1921); p. 135 View in Reaxys

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O

N

O

O

O O

O O

O

N-phenyl-<2.4.5-trimethoxy-benzaldehyde >-isoox‐ ime

N N

O

O

Rx-ID: 7456263 View in Reaxys 35/37 Yield

Conditions & References im Dunkeln Alessandri; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 24 I; (1915); p. 63; Gazzetta Chimica Italiana; vol. 51 II; (1921); p. 135 View in Reaxys

O Z O O

O

O

O

O

O

E

O

Z

O

O

E

O

O

O

O

O

O

O

O O

O

O O

O

Rx-ID: 2021143 View in Reaxys 36/37 Yield

Conditions & References

1.18 g, 0.28 g, 0.26 g, 0.19 g, 46 mg

Time= 720h, Irradiation, Mechanism Saxena, D. B.; Mukerjee, S. K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 24; (1985); p. 683 - 684 View in Reaxys

O O

O

O

Rx-ID: 7186251 View in Reaxys 37/37 Yield

Conditions & References Sanchez-Viesca; Ciencia (Mexico City); vol. 25; (1966); p. 25; ; vol. 66; nb. 28475 View in Reaxys Patent; Hoffmann-La Roche; NL6514178; (1966); ; vol. 65; nb. 12214g; (1966) View in Reaxys Sharma et al.; Journal of Pharmaceutical Sciences; vol. 53; (1964); p. 1055 View in Reaxys Godfrey et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1974); p. 1353 View in Reaxys Fujita; Yamaskita; Yuki Gosei Kagaku Kyokaishi; vol. 31; (1973); p. 839 View in Reaxys Sharma; Dandiya; Indian Journal of Applied Chemistry; vol. 32; (1969); p. 236 View in Reaxys Garofano; Werber; Annali di Chimica (Rome, Italy); vol. 50; (1960); p. 245,271-275 View in Reaxys

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wherein the compound of Formula I is selected from the group consisting of ...

4-benzyloxy-benzaldehyde; 4-acetoxy-3,5-dimethoxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-carboxyl-3,4-dimethoxybenzaldehyde; 2,4,5-trimethoxybenzaldehyde; 3-chloro-4-methoxybenzaldehyde; 3-butyloxy-4-methoxybenzaldehyde; 3,5-dimethoxy-4-benzoxybenzaldehyde; ...

Patent; Engles, Charles R.; Fuller, Bryan; Pilcher, Brian Keith; US2003/124157; (2003); (A1) English View in Reaxys

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