Dichloromethane → Phenylpropiolic Acid

Participants

Reaction Steps

Phenylpropiolic acid was synthesized according to the method as described in J. Chem. Soc., Vol. 83, page 1154. To a mixture of 42 g of phenylpropiolic acid and 50 ml of methylene chloride was added 42 ml of thionyl chloride, and the mixture was mildly refluxed by heating on a water bath. After the completion of the generation of gas, the solvent and excessive thionyl chloride were distilled off under reduced pressure. The pale yellow liquid thus obtained was gradually added to 300 ml of methanol under cooling with ice. After being allowing to stand overnight, the solvent was distilled off under a reduced pressure, and the residual liquid was washed with water and dried to obtain 44.5 g of almost pure methyl phenylpropiolate.

Provenance & Evidence