反应详情

温度

15 °C

To a solution of methyl 3,5-dihydroxybenzoate (50 g, 0.30 mol) in DMF (500 ml) at 0° C. was added sodium hydride (10.8 g, 0.27 mol) portion wise. The reaction was allowed to warm to 15° C., and stirred for 20 minutes. The mixture was re-cooled to 0° C. and a solution of 2-methylbenzyl bromide (36 ml, 0.27 mol) in DMF (50 ml) was added over 30 minutes. The reaction was warmed to ambient temperature and concentrated in vacuo. The residual oil was partitioned between ethyl acetate (500 ml) and water (250 ml), and the ethyl acetate layer was separated, washed with water and evaporated. The residue was purified by column chromatograph on silica gel (gradient, 0-100% ethyl acetate in isohexane) to give the desired compound (21.9 g, 27%).

1. temperatureThe mixture was re-cooled to 0° C.
2. temperatureThe reaction was warmed to ambient temperature
3. concentrationconcentrated in vacuo
4. customThe residual oil was partitioned between ethyl acetate (500 ml) and water (250 ml)
5. customthe ethyl acetate layer was separated
6. washwashed with water
7. customevaporated
8. customThe residue was purified by column chromatograph on silica gel (gradient, 0-100% ethyl acetate in isohexane)