Sodium Hydroxide → 3-Methyl-2-(2-methyl-1-propenyl)benzoic acid

Participants

Reaction Steps

A solution of the 3-methyl-2-(2-methyl-1-propenyl)benzoic acid ethyl ester (290) (3 g-0.014 mol) in MeOH (50 mL) is treated with 2N NaOH (10 mL) and refluxed for 6 h. The solvent is removed in vacuo and the residue diluted with water (75 mL). The aqueous phase is extracted with EtOAc (30 mL) and then separated and acidified to pH 2-3 with concentrated HCl. The solid precipitated is extracted into EtOAc (3×50 mL). The extracts are washed with water (2×30 mL) and brine (2×30 mL), and dried over MgSO4 and concentrated in vacuo to give the product as white solid (2.0 g, 75%).

Provenance & Evidence