1-(4-Fluorophenyl)cyclohexane-1-carboxylic acid → (1-(4-Fluorophenyl)cyclohexyl)methanol

HRID 1506292Notes

Reaction equation

HRID 1506292 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14](O)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 7361361-(4-Fluorophenyl)cyclohexane-1-carboxylic acid

Product 1

HCID 66685762(1-(4-Fluorophenyl)cyclohexyl)methanolYield 109.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1 M solution of borane-THF complex (16.7 mL, 16.7 mmol) was slowly added to a solution of (1-(4-fluorophenyl)cyclohexane carboxylic acid (928 mg, 4.18 mmol) in THF (15 mL) at room temperature under a nitrogen atmosphere. After 20 min., the reaction mixture was refluxed for 16 hrs, cooled to room temperature and quenched by the dropwise addition of 1N HCl until further addition caused no more gas evolution. Ethyl acetate and 1N sodium hydroxide were added. The organic layer was washed with 1N sodium hydroxide (2×), brine, dried over sodium sulfate, filtered, and evaporated in vacuo to yield the (1-(4-fluorophenyl)cyclohexyl)methanol (950 mg, 100% yield) as a light tan oil containing some solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 16 hrs
  2. customquenched by the dropwise addition of 1N HCl until further addition
  3. additionEthyl acetate and 1N sodium hydroxide were added
  4. washThe organic layer was washed with 1N sodium hydroxide (2×), brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c025e232b404bbaab5a5902789614ea
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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