4-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)phenol → 4-(2-Hydroxy-1,1,1-trifluoro-2-propyl)cyclohexanol

HRID 1419794Notes

Reaction equation

HRID 1419794 reaction equation
[OH:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)([CH3:7])[C:3]([F:6])([F:5])[F:4]>C(O)(C)C.Cl.[Rh]>[OH:1][C:2]([CH:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)([CH3:7])[C:3]([F:4])([F:5])[F:6]

Participants

5

Reactant 1

HCID 544399464-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)phenol

Product 1

HCID 539089674-(2-Hydroxy-1,1,1-trifluoro-2-propyl)cyclohexanol

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

18.9 g (0.092 mol) of 4-(2-hydroxy-1,1,1-trifluoro-2-propyl)phenol were hydrogenated in a mixture of 200 ml of isopropanol and 6 ml of concentrated hydrochloric acid in the presence of 2.3 g of rhodium (5% on charcoal) at 150 bar and 50° C. After filtration to remove the catalyst and concentration, 18.8 g (96.6% of theory) remained of a colorless product.

Workup

  1. filtrationAfter filtration
  2. customto remove
  3. concentrationthe catalyst and concentration, 18.8 g (96.6% of theory)

Sources & evidence

ORD record
ord-d0d4752887c24f14bb1f64ec4d666a79
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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