Hydrochloric Acid → 1-(trifluoromethyl)cyclohexanol

HRID 2371597Notes

Reaction equation

HRID 2371597 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:8][C:9]([Si](C)(C)C)([F:11])[F:10].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl.[SiH3]O[SiH3]>O1CCCC1>[F:8][C:9]([F:11])([F:10])[C:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 123318DisiloxaneHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 112752281-(trifluoromethyl)cyclohexanolYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

K. Prakash, et al., J. Am. Chem. Soc., Vol. 111, 393-395 (1989) describe the reaction of the fluoride ion catalyzed reaction of trifluoromethyltrimethylsilane with ketones and aldehydes to give the corresponding α-trifluoromethyl substituted alcohol and trimethylfluorosilane. In a typical reaction, cyclohexanone was reacted with trifluoromethyltrimethylsilane in tetrahydrofuran in the presence of tetrabutylammonium fluoride at 0° C. After 1 hour, the solution was mixed with 0.5 N HCl to hydrolyze the intermediate silyl ether, and then the product was isolated by distillation. In this case, a 77% yield of 1-trifluoromethylcyclohexanol is reported.

Workup

  1. customthe product was isolated by distillation

Sources & evidence

ORD record
ord-1c5254d82ffa4288bb2a3bd0e0fa0598
Source dataset
uspto-grants-1992_03
Patent number
US05093512

Reaction notes

Loading…