反应详情

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+).

1. customThe resulting reaction mixture
2. temperatureto reflux under nitrogen for 2.5 h
3. washthe organic layer was washed with 0.1 N HCl (3×30 mL), 5% NaHCO3 solution (1×30 mL) and brine (1×30 mL)
4. customUpon drying
5. filtration(MgSO4), filtration of the drying agent and concentration
6. customthe resulting oily residue was chromatographed on silica gel (30% ethyl acetate/hexane)