Hydrochloric Acid → 4,4-Difluorocyclohexane-1-carbaldehyde

Temperature

-65 °C

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%).

1. additionwas added at −40° C.
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with toluene
4. washthe combined organic layers were washed with 1 N hydrochloric acid, saturated sodium hydrogencarbonate aqueous solution and saturated sodium chloride aqueous solution in order
5. dry with materialdried with anhydrous magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. distillationthe obtained oily residue was subjected to distillation under reduced pressure (55-57° C./6 mmHg)

ORD record

ord-32d73b297bd6437999d7d64c4e5a8631

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321747B2