反应详情

A solution of ethyl 2,6-dimethyl-3-(1-methylethyl)benzoate (2.8 g) in dry 1,2-dimethoxyethane (40 ml) was added dropwise under a nitrogen atmosphere to a stirred solution of lithium aluminum hydride in dry 1,2-dimethoxyethane (80 ml) at approximately -78°. The mixture was allowed to warm to ambient temperature. The mixture was heated to reflux and maintained under reflux for one hour. After cooling to ambient temperature, a solution of 1,2-dimethoxyethane (20 ml) in water (5 ml) was added dropwise to the reaction mixture, followed by additional water (25 ml). The reaction mixture was acidified with 3 N hydrochloric acid and extracted with diethyl ether. The combined ether extracts were dried over magnesium sulfate, filtered, and the solvent evaporated to give [2,6-dimethyl-3-(1-methylethyl)phenyl]methanol (1.7 g). The nmr spectrum was consistent with the proposed structure.

1. temperatureThe mixture was heated
2. temperatureto reflux
3. temperaturemaintained
4. temperatureunder reflux for one hour
5. temperatureAfter cooling to ambient temperature
6. extractionextracted with diethyl ether
7. dry with materialThe combined ether extracts were dried over magnesium sulfate
8. filtrationfiltered
9. customthe solvent evaporated