Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate → HCID 59509487, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of formic acid (12 mL) and 4-hydroxy-3-(2-methylprop-2-enyl)benzoic acid ethyl ester (4.8 g, 0.022 mol) is heated at 110° C. for 15 minutes. The reaction mixture is cooled to room temperature and formic acid is removed under reduced pressure. Demineralized water is added to the residue and the aqueous layer is extracted with dichloromethane (3×15 mL). Combined organic layers are washed with demineralized water (1×15 mL) followed by brine (1×15 mL) and dried over sodium sulphate. Removal of solvent gives a viscous liquid which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate, 90:10) to give 2,2-dimethyl-2,3-dihydro-1-benzofuran-5-carboxylic acid ethyl ester.

Provenance & Evidence