Phenylacetic Acid → HCID 2733559, compound

Participants

Reaction Conditions

Reaction Steps

A solution of butyllithium in hexane (0.4 mol, 250 ml of 1.6 M solution) was added to a solution of 40 g (0.4 mol) of diisopropylamine in 300 ml of tetrahydrofuran cooled in an ice-bath. A solution of 27.23 g (0.2 mol) of benzeneacetic acid in 200 ml of tetrahydrofuran was added near 0° C. and the reaction mixture was stirred for 30 minutes at 0° C. A 100 g portion of trimethylchlorosilane was added, the mixture was warmed to room temperature, stirred for 1.5 hours, and then filtered under nitrogen. The filtrate was evaporated to dryness under reduced pressure; the residue was dissolved in 80 ml of diethyl ether and filtered. The filtrate was evaporated to dryness and then distilled to give 37.2 g of β,β-[bis(trimethylsiloxy]styrene as a colorless liquid: bp 95° C. (0.5 mm).

Provenance & Evidence