p-Tolylacetic acid → HCID 13331672, compound

Participants

Reaction Steps

To a stirred solution of 4-methylphenylacetic acid (20.6 g, 137 mmol) in methylene chloride (100 mL) in a pressure flask cooled on a dry-acetone bath was added isobutene (190 mL) followed by concentrated sulfuric acid (2.5 mL). After 36 hours, the mixture was cooled (dry ice/acetone bath) and isobutene was removed in a slow stream of nitrogen. The residue was treated with 10% NaHCO3, and extracted with methylene chloride (3×100 mL). The combined methylene chloride extract was washed with 10% NaHCO3 and brine, and dried (Na2SO4). Evaporation of the solvent gave t butyl 4-methylphenylacetate as a colorless oil (25 g, 90%).

Provenance & Evidence