Water → 4-Vinylcyclohexyl formic acid methyl ester

Participants

Reaction Steps

To a mixture of 25.2 g (70.5 mmol) of methyltriphenylphosphonium bromide with 125 ml of tetrahydrofuran (THF) was added 7.9 g (70.5 mmol) of potassium-tert-butoxide (t-BuOK) while being kept at a temperature lower than −20° C. and stirred at the same temperature for 1 hour. Then, 50 ml of solution of 10.0 g (58.8 mmol) of methyl 4-formylcyclohexanecarboxylate in THF was added dropwise to the reaction solution while being kept at a temperature lower than −20° C. and stirred at the same temperature for 2 hours. After finishing of the reaction, 50 ml of water was added to the reaction mixture and then the product was extracted with 200 ml of toluene. The organic layer thus obtained was washed with water thrice and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (eluent: toluene) to obtain 6.8 g of a crude methyl 4-vinylcyclohexanecarboxylate.

Provenance & Evidence