反应详情

温度

-20 °C

6.3 ml of a 2 molar solution of isopropylmagnesium chloride in THF (12 mmol) were added dropwise to a solution of 3 g methyl 4-iodobenzoate (11.5 mmol) in 30 ml THF at a temperature of −20° C. The reaction mixture was stirred for 1.5 h at −20° C., then 1.26 ml acetone (17 mmol) were added and the mixture was allowed to warm to rt. After 30 min at ambient temperature the reaction was quenched with methanol, poured into water and extracted with EtOAc. The combined extracts were washed with brine, dried with magnesium sulfate, filtered and concentrated. Chromatographic purification (silica gel; c-hexane/EtOAc 2:1) of the remaining residue yielded 1.64 g (74%) of 4-(1-hydroxy-1-methyl-ethyl)-benzoic acid methyl ester as a colorless liquid. 1H-NMR (CDCl3, 300 MHz): δ 1.60 (s, 6H), 3.91 (s, 3H), 7.56 (d, J=9 Hz, 1H), 8.01 (d, J=9 Hz, 1H).

1. temperatureto warm to rt
2. customAfter 30 min at ambient temperature the reaction was quenched with methanol
3. additionpoured into water
4. extractionextracted with EtOAc
5. washThe combined extracts were washed with brine
6. dry with materialdried with magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customChromatographic purification (silica gel; c-hexane/EtOAc 2:1) of the remaining residue