Dichloromethane → Allyl 4-hydroxymethylbenzoate

Participants

Reaction Steps

To a solution of 4-hydroxymethylbenzoic acid (0.5 g, 3.3 mmol) in CHCl3 (10 mL) was added allyl bromide (0.6 mL, 0.84 g, 6.9 mmol) and diisopropylethylamine (1.3 mL, 0.96 g, 7.5 mmol). The resulting reaction mixture was allowed to reflux under nitrogen for 2.5 h. Upon cooling to rt, dichloromethane (50 mL) was added and the organic layer was washed with 0.1 N HCl (3×30 mL), 5% NaHCO3 solution (1×30 mL) and brine (1×30 mL). Upon drying (MgSO4), filtration of the drying agent and concentration, the resulting oily residue was chromatographed on silica gel (30% ethyl acetate/hexane) to give 440 mg (70%) of a colorless oil. 1H NMR (CDCl3) 8.06 (d, J=8.2 Hz, 2H), 7.44 (d, J=8.2 Hz, 2H), 6.11-5.98 (m, 11H), 5.42 (dd, J=17.2, 1.5 Hz, 11H), 5.30 (dd, J=10.4, 1.2 Hz, 1H), 4.83 (dd, J=5.6, 1.2 Hz, 2H), 4.78 (s, 2H), 1.80 (br s, 1H). MS 192 (M+).

Provenance & Evidence