1-Cyclohexyl-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene → [4-Cyclohexyl-3-(trifluoromethyl)phenyl]methanol

HRID 1828703

Reaction equation

HRID 1828703 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][O:14]CC3C=CC(OC)=CC=3)=[CH:9][C:8]=2[C:24]([F:27])([F:26])[F:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl.CCOC(C)=O>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:8]=2[C:24]([F:25])([F:26])[F:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 220577361-Cyclohexyl-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene

Product 1

HCID 22057748[4-Cyclohexyl-3-(trifluoromethyl)phenyl]methanol

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The obtained 1-cyclohexyl-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene is dissolved in a mixture of TFA and DCM (8 mL, 1:1 v/v). After stirring at room temperature for 2 h, all volatile materials are evaporated and the residue obtained is dissolved in EtOAc and washed with saturated aqueous NaHCO3. The organic layer is separated, washed with saturated aqueous NaCl and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (20% ethyl acetate in hexanes) to give (4-cyclohexyl-3-trifluoromethyl-phenyl)-methanol as a colorless oil.

Workup

  1. customall volatile materials are evaporated
  2. customthe residue obtained
  3. washwashed with saturated aqueous NaHCO3
  4. customThe organic layer is separated
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration
  8. customthe residue is purified by silica gel chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0a86972aced5457e8484d1df143603d7
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Linked notes

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