Benzyl Chloride → Benzyl 2-cyanoacetate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.7 g (0.02 mol) of cyanoacetic acid, 0.8 g (0.02 mol) of sodium hydroxide, 7.60 g (0.06 mol, 3 equivalents) of benzyl chloride and 0.64 g (2.0 mmol) of tetrabutylammonium bromide in 15 ml of tert-butyl methyl ether/water (v:v=2:1 ) was stirred at 100° C. (oil bath temperature 110° C.) for 3 h. The pH of the aqueous phase was then adjusted from 0.2 to 6.3 using 3.15 g of 1 M aqueous sodium hydroxide solution, the organic phase was separated off and the aqueous phase was extracted with tert-butyl methyl ether (2×5 ml). The combined organic phases was dried with sodium sulfate and analyzed by gas chromatography. 2.45 g (70 percent) of benzyl cyanoacetate was obtained.

Provenance & Evidence