Triethylamine → Methyl 2-(benzyloxy)-5-(dimethoxymethyl)benzoate

Reaction equation

[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8](C=O)[CH:7]=[CH:6][C:5]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:21]([O:26][CH3:27])([O:24][CH3:25])OC.C(N(CC)CC)C>CO>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH:21]([O:24][CH3:25])[O:26][CH3:27])[CH:7]=[CH:6][C:5]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Procedure

39.1 g of 2-benzyloxy-5-formylbenzoic acid methyl ester was dissolved in 300 ml of methanol. 60 ml of trimethyl orthoformate and 2 g of p-tosylic acid were added thereto, and the solution was heated under refluxed for 4 hours. After the solution was cooled down to room temperature, 5 ml of triethylamine was added thereto, and the solution was evaporated. The residue was dissolved in ethyl acetate, and the solution was successively washed with water and saturated sodium bicarbonate water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated, to give 39.08 g of 2-(benzyloxy)-5-(dimethoxymethyl)benzoic acid methyl ester.