Benzoic Acid → Ethyl cyclopropylideneacetate

Participants

Reaction Conditions

Reaction Steps

A suspension of 38.49 g (220.80 mmol) of [(1-ethoxycyclopropyl)oxy](trimethyl)silane, 100.0 g (287.04 mmol) of ethyl (triphenylphosphoranylidene)acetate and 3.51 g (28.70 mmol) of benzoic acid in 600 ml of toluene is stirred at a bath temperature of 90° C. for 18 hours. After cooling, the mixture is poured onto 800 g of silica gel 60 and eluted successively with in each case 3 liters of petroleum ether 40-60 and dichloromethane. The dichloromethane eluate is, after removal of the solvent, distilled at 160° C. and 14 mbar in a kugelrohr. This gives 17.95 g (64% of theory) of the title compound as a colorless liquid.

Provenance & Evidence