Water → Methyl alpha-(2-methoxymethylphenyl)-beta-methylacrylate

Participants

Reaction Conditions

Reaction Steps

37.1 g (100 mmol) of ethyltriphenylphosphonium bromide are introduced under nitrogen into 300 ml of absolute tetrahydrofuran. At 5° C., 11.2 g (0.1 mol) of potassium t-butanolate are added. After stirring at 5° C. for one hour, 20.8 g (100 mmol) of methyl 2-methoxymethylphenylglyoxylate in 100 ml of tetrahydrofuran are added dropwise. The mixture is stirred at 5° C. for one hour and at 25° C. for one hour, 200 ml of water are added, the mixture is extracted with methylene chloride and the organic phases are washed with water. After drying over sodium sulfate, the solvent is removed under reduced pressure. The residue is purified by chromatography on a silica gel column (methyl tert-butyl ether/n-hexane=1/2). 17.2 g (78%) of the abovementioned ester are obtained as an oil (Z/E isomer=1/9).

Provenance & Evidence