Sodium Hydroxide → Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate

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Reaction Steps

A mixture of 4-(2-methylprop-2-enyloxy)benzoic acid ethyl ester (15 g) and 1-methyl-2-pyrrolidinone (150 mL) is heated at reflux for nine hours. The reaction mixture is cooled to room temperature and made basic (pH ˜10) by using aqueous sodium hydroxide solution. The aqueous layer is washed with toluene (2×20 mL) and then made acidic (pH ˜2) with 2N HCl. The aqueous layer is extracted with ethyl acetate (3×20 mL). Combined organic layers are washed with brine (1×15 mL) and dried over sodium sulphate. Removal of solvent gives a dark brown liquid which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate, 80:20) to give 4-hydroxy-3-(2-methylprop-2-enyl)benzoic acid ethyl ester.

Provenance & Evidence