4-Phenyl-cyclohexanecarboxylic acid → (4-Phenylcyclohexyl)methanol

HRID 480253

Reaction equation

HRID 480253 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([CH:13]2[CH2:18][CH2:17][CH:16]([C:19](O)=[O:20])[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:7]1([CH:13]2[CH2:18][CH2:17][CH:16]([CH2:19][OH:20])[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 3448124-Phenyl-cyclohexanecarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 3100608(4-Phenylcyclohexyl)methanolYield 136%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of LiAlH4 (0.56 g, 14.8 mmol, 2.0 equiv) was prepared under argon in 50 mL of anhydrous THF (50 mL) kept at 0° C. A solution of 4-phenyl-cyclohexanecarboxylic acid (1.5 g, 7.34 mmol, 1.0 equiv) in 50 mL of THF was added dropwise over a 20 min period. The reaction mixture was stirred at ambient temperature for 1.5 h and then cooled to 0° C. The excess hydride reagent was carefully quenched under argon by dropwise addition of 1 N HCl. After quenching, the reaction mixture was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to give the title product as a colorless oil (1.9 g crude) which was used without further purification.

Workup

  1. customkept at 0° C
  2. temperaturecooled to 0° C
  3. customThe excess hydride reagent was carefully quenched under argon by dropwise addition of 1 N HCl
  4. customAfter quenching
  5. extractionthe reaction mixture was extracted with EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-56cd780c090840b79dbc6643f62ad871
Source dataset
uspto-grants-2003_11
Patent number
US06649642B2

Linked notes

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