反应详情

A solution of 4-isopropyl-3-methylphenol (10.0 g, 67 mmol), methyl bromoacetate (6.6 mL, 70 mmol) and anhydrous potassium carbonate (10.1 g, 73 mmol) in 2-butanone (100 mL) was heated to reflux for 20 h. The mixture was cooled and partitioned between water (350 mL) and ethyl acetate (100 mL). The organic phase was washed with brine, and the aqueous phases were back-extracted in sequence with more ethyl acetate. The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford sufficiently pure product, methyl 2-(4 isopropyl-3-methylphenoxy)acetate, as an oil (15.0 g, 67 mmol, 100%). 1H NMR (CDCl3, 300 MHz): δ 7.05 (1H, d, J=9.3 Hz), 6.64–6.58 (2H, m), 4.51 (2H, s), 3.71 (3H, s), 2.98 (1H, m, J=7.0 Hz), 2.22 (3H, s), 1.11 (6H, d, J=7.0 Hz).

1. temperatureto reflux for 20 h
2. temperatureThe mixture was cooled
3. custompartitioned between water (350 mL) and ethyl acetate (100 mL)
4. washThe organic phase was washed with brine
5. extractionthe aqueous phases were back-extracted in sequence with more ethyl acetate
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customevaporated