反应 #719784

反应方程式

hydrochloric acid

ammonium chloride

4,4-difluorocyclohexanecarboxylic acid ethyl ester

diisobutyl aluminum hydride toluene

→

title compound

收率 57.0%

4,4-Difluorocyclohexanecarboaldehyde

收率 57.0%

溶剂

toluene

反应条件

后处理

1. 1
   workup.ADDITIONwas added at −40° C.
2. 2
   其他The organic layer was separated
3. 3
   萃取the aqueous layer was extracted with toluene
4. 4
   洗涤the combined organic layers were washed with 1 N hydrochloric acid, saturated sodium hydrogencarbonate aqueous solution and saturated sodium chloride aqueous solution in order
5. 5
   干燥dried with anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   workup.DISTILLATIONthe obtained oily residue was subjected to distillation under reduced pressure (55-57° C./6 mmHg)

实验过程

To a solution of 173 g (0.900 mol) of 4,4-difluorocyclohexanecarboxylic acid ethyl ester in 1.0 L toluene, 945 ml (0.945 mol) of 1.0 M diisobutyl aluminum hydride-toluene solution was added dropwise at −55° C. or lower temperatures and then the reaction solution was stirred at −65° C. for 30 minutes. After completion of the reaction, saturated ammonium chloride aqueous solution was added at −40° C. or lower temperatures to the reaction solution and then 1.0 L of 4 N hydrochloric acid was added at 0° C. or lower temperatures. The organic layer was separated and then the aqueous layer was extracted with toluene, and the combined organic layers were washed with 1 N hydrochloric acid, saturated sodium hydrogencarbonate aqueous solution and saturated sodium chloride aqueous solution in order and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained oily residue was subjected to distillation under reduced pressure (55-57° C./6 mmHg) to provide 75.3 g of the title compound as a colorless oil (yield: 57%).

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