Water → 4-Vinylcyclohexyl formic acid methyl ester

Participants

Reaction Steps

297.4 g of methoxymethyltriphenylphosphonium bromide was dispersed in 900 mL of tetrahydrofuran (THF) and 95.6 g potassium t-butoxide was added at −8° C. in 3 minutes. After stirring for 30 minutes, all of methyl 4-formylcyclohexanecarboxylate was dissolved in 270 mL of THF and the resulting solution was added dropwise at −6 to 4° C. over 50 minutes. After stirring at 0 to 4° C. for 30 minutes, 15 mL of water was added. The solvent of the reaction mixture was distilled off under reduced pressure and 500 mL of hexane was added, followed by stirring at room temperature for 30 minutes. The precipitate was filtered and the precipitate was suspended and washed again with 500 mL of hexane. After combining with the hexane filtrate, the mixture was washed in turn with a mixed solution of methanol and water (1:1), water, and saturated saline. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 81.2 g of an oily substance. The oily substance was distilled under reduced pressure to obtain 57.3 g of methyl 4-vinylclohexanecarboxylate. A boiling point was 122 to 127° C./48 hPa. The gas chromatography analysis revealed that, the resulting substance is a mixture of a cis isomer and a trans isomer in a mixing ratio of 26:74.

Provenance & Evidence