Phenylacetic Acid → HCID 19431592, compound

Participants

Reaction Steps

Lithium diisopropylamide (450 ml of a 1.5M solution in cyclohexane) was added to a stirred solution of phenylacetic acid (40.8 g) in tetrahydrofuran (300 ml) at between 0° and 5° C. The mixture was warmed to room temperature, stirred for 1.5 hours, treated with 2-chloroethylmethylsulphide (30 ml) in tetrahydrofuran 30 ml, refluxed for 2 hours, cooled and evaporated. To the residue in methanol (200 ml) was added concentrated sulphuric acid (50 ml) in methanol (250 ml), the mixture refluxed for 1.5 hours, and evaporated. The residue was partitioned between water and chloroform, the organic layer washed with aqueous 10% potassium carbonate, dried over sodium sulphate and evaporated to give a light brown oil (55 g). A portion of this (33 g) was distilled to give the title compound (24.5 g, 61%) as a clear liquid b.p. 128°-135° C. at 5 mm Hg.

Provenance & Evidence