2,4,5-三甲氧基苯甲醛合成路线 （共 90 条）
反应条件
1: nitric acid / water / -10 °C 2: palladium 10 on activated carbon; hydrogen / methanol; ethyl acetate / 15 h / 20 °C / Inert atmosphere View Scheme
参考文献
Donohoe, Timothy J.; Jones, Christopher R.; Kornahrens, Anne F.; Barbosa, Luiz C. A.; Walport, Louise J.; Tatton, Matthew R.; O'Hagan, Michael; Rathi, Akshat H.; Baker, David B.
Journal of Organic Chemistry, 2013 , vol. 78, # 24 p. 12338 - 12350
反应条件
1: mCPBA / 2 h / Ambient temperature
2: aq. KOH / ethanol / 2 h / 50 °C
3: 94 percent / NaH / dimethylformamide / 1 h / Ambient temperature
4: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight
5: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h
View Scheme
参考文献
ARIZONA BOARD OF REGENTS, A BODY CORPORATE OF THE STATE OF ARIZONA, ACTING FOR AN ON BEHALF OF ARIZONA STATE UNIVERSITY; MADATHIL, Manikandadas, Mathilakathu; KHDOUR, Omar; HECHT, Sidney
Patent: WO2014/59158 A1, 2014 ;
反应条件
1: 87 percent / BBr3 / CH2Cl2 / 16 h / 20 °C
2: 54 percent / bromine; NaOAc; acetic acid / 2 h / 20 °C
View Scheme
参考文献
Pereira, Alban R.; Strangman, Wendy K.; Marion, Frederic; Feldberg, Larry; Roll, Deborah; Mallon, Robert; Hollander, Irwin; Andersen, Raymond J.
Journal of Medicinal Chemistry, 2010 , vol. 53, # 24 p. 8523 - 8533
反应条件
nitric acid
T=-5°C; 0.5 h;
参考文献
Downer, Nadale K.; Jackson, Yvette A.
Organic and Biomolecular Chemistry, 2004 , vol. 2, # 20 p. 3039 - 3043
参考文献
van Alphen
Recueil des Travaux Chimiques des Pays-Bas, 1927 , vol. 46, p. 198
Recueil des Travaux Chimiques des Pays-Bas, 1928 , vol. 47, p. 174
反应条件
1: NaClO2, NH2SO3H
3: selective mono-demethylation
View Scheme
参考文献
Rama Rao; Yadav; Kishta Reddy; Upender, Velaparthi
Tetrahedron Letters, 1991 , vol. 32, # 38 p. 5199 - 5202
反应条件
1: 0.16 g
2: 20 mg / DDQ
View Scheme
参考文献
Iinuma; Iwashima; Matsuura
Chemical and Pharmaceutical Bulletin, 1984 , vol. 32, # 12 p. 4935 - 4941
反应条件
1: 80percent aq. KOH / ethanol / 24 h
3: 30percent H2O2, 5percent aq. NaOH / methanol; acetone / Ambient temperature
4: BF3 etherate / benzene / 3 h / Ambient temperature
5: conc. HCl / acetic acid / 2 h / boiling water bath
6: K2CO3, KI / dioxane / 20 h / Heating
View Scheme
参考文献
Pathak, V. P.; Saini, T. R.; Khanna, R. N.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984 , vol. 23, # 1 p. 89 - 90
反应条件
1: mCPBA / 2 h / Ambient temperature
2: aq. KOH / ethanol / 2 h / 50 °C
3: 94 percent / NaH / dimethylformamide / 1 h / Ambient temperature
4: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight
5: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h
View Scheme
参考文献
Poigny, Stephane; Guyot, Michele; Samadi, Mohammad
Tetrahedron, 1998 , vol. 54, # 49 p. 14791 - 14802
反应条件
1: NaClO2, NH2SO3H
3: selective mono-demethylation
4: K2CO3 / dimethylformamide
5: aq. Na2S2O4
6: K2CO3 / acetone / 6 h / Heating
7: aq. KOH / ethanol / 10 h / 25 °C
8: PPE / CHCl3 / 36 h / 25 °C
9: aq. KOH / ethanol / 8 h / 25 °C
11: PCC / CH2Cl2 / 15 h / 25 °C
12: 82 percent / K2CO3 / methanol / 36 h / 25 °C
13: 95 percent / ceric ammonium nitrate / acetonitrile; H2O
14: 85 percent / Et3N*BCl3 / CH2Cl2 / 0.25 h / 0 °C
View Scheme
参考文献
Rama Rao; Yadav; Kishta Reddy; Upender, Velaparthi
Tetrahedron Letters, 1991 , vol. 32, # 38 p. 5199 - 5202
