Toluene → HCID 18921242, compound

Participants

Reaction Steps

A stirred mixture of 2.91 g (20 mmol) of 4-vinylbenzoic acid, 5.84 g (22 mmol) of 1-octadecanol, 0.17 g (1 mmol) of 4-toluenesulfonic acid, and 75 ml of toluene was heated at reflux with water separated azeotropically using a Dean-Stark trap. After 16 hours, the mixture was cooled to ambient temperature and filtered through a short column of basic alumina, eluting with tetrahydrofuran. The filtrate was concentrated to deposit a solid product, which was purified by chromatography on silica gel (a heptane/dichloromethane eluate), followed by recrystallization from acetonitrile. A white solid was obtained, mass 3.98 g (51% yield).

Provenance & Evidence