Ethanol → 4,4-Difluorocyclohexan-1-ol

HRID 1674422Notes

Reaction equation

HRID 1674422 reaction equation
C([O:9][CH:10]1[CH2:15][CH2:14][C:13]([F:17])([F:16])[CH2:12][CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[Na+].C(O)C.C(OCC)(=O)C>O>[F:16][C:13]1([F:17])[CH2:14][CH2:15][CH:10]([OH:9])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59469432Cyclohexanol, 4,4-difluoro-, 1-benzoate

Product 1

HCID 5463004,4-Difluorocyclohexan-1-olYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4,4-difluorocyclohexyl benzoate (2.0 g), 1M sodium hydroxide solution (10 mL) and ethanol (20 mL) was stirred at 70° C. for 3 hr. The reaction mixture was added to a mixture of ethyl acetate and water, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was successively washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (1.0 g, 90%).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layer was successively washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-26b9004031764aea95041fbecca14c2b
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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