反应详情

To a suspension of benzoic acid allyl ester (100 g, 0.617 mol) and zinc (activated Zn) (161 g, 2.47 mol) in diethyl ether (1.23 L) was added dropwise a solution of trichloroacetyl chloride (223 g, 1.23 mol) and dimethoxyethane (110 g, 1.23 mol) in diethyl ether (1.23 L, 2 L/mol) over 40 minutes under nitrogen with vigorously stirring, and then the mixture was stirred at room temperature (internal temperature: 30° C.) for 29 hours. During the stirring, additional zinc (activated Zn) (respectively, 150 g (2.29 mol) and 100 g (1.53 mol)) was added at 7 and 24 hours after the beginning of the stirring. To the reaction mixture was added hexane (1 L), and the mixture was stirred for 10 minutes, and then the solid was removed by decantation and the supernatant was washed with water (1 L), aqueous saturated sodium bicarbonate solution (3×1 L) and saturated saline (500 mL), and dried over magnesium sulfate. The mixture was evaporated and the precipitated white solid was collected by filtration and washed with hexane (500 mL) to give the titled compound (62.5 g, 37%).

1. stirringthe mixture was stirred at room temperature (internal temperature: 30° C.) for 29 hours
2. stirringthe mixture was stirred for 10 minutes
3. customthe solid was removed by decantation
4. washthe supernatant was washed with water (1 L), aqueous saturated sodium bicarbonate solution (3×1 L) and saturated saline (500 mL)
5. dry with materialdried over magnesium sulfate
6. customThe mixture was evaporated
7. filtrationthe precipitated white solid was collected by filtration
8. washwashed with hexane (500 mL)