Trimethyl orthoformate → (E)-3-(4-dimethoxymethylphenyl)acrylic Acid

Participants

Reaction Conditions

Reaction Steps

38.81 mL (0.354 mmol) of trimethylorthoformate is added to a suspension of 25 g (0.141 mol) of (E)-3-(4-formylphenyl)acrylic acid in 350 mL of methanol and the mixture is refluxed for 48 hours. After cooling, the reaction mixture is filtered and the filtrate is evaporated down. The residue is taken up in 500 mL of dichloromethane and filtered through CELITE® filter aid. The filtrate is evaporated down to 150 mL and cooled to 0° C. The precipitate formed is filtered off, washed with dichloromethane/petroleum ether (1:1), and dried at 60° C. in the circulating air dryer. Yield: 12.05 g (31.5% of theory); C12H14O4 (M=222.24); calc.: molecular ion peak (M+H)+: 245; found: molecular ion peak (M+H)+: 245; Rf value: 0.6 (silica gel, petroleum ether/ethyl acetate (1:1)).

Provenance & Evidence