Methyl 4-Formylbenzoate → 4-[2-(4,4-Dimethyl-chroman-6-yl)-propenyl]-benzoic acid methyl ester

Participants

Reaction Steps

A solution of 2.0 g (3.8 mmol) of 1-(4,4-dimethyl-6-chromanyl)ethyltriphenylphosphonium bromide and 630 mg (3.8 mmol) of methyl 4-formylbenzoate in 100 ml of 1,2-epoxybutane was heated under reflux for 72 hours. The reaction mixture was then concentrated in vacuo to an oil. The oil was purified by column chromatography on silicic acid, eluting with ether-hexane (1:9). This afforded mg (27% yield) of the title compound as a solid, mp 92°-95° C.

Provenance & Evidence