1-Phenylcyclohexane-1-carboxylic acid → 1-Phenylcyclohexanemethanol

HRID 1430228Notes

Reaction equation

HRID 1430228 reaction equation
[C:1]1([C:7]2([C:13](O)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1.C(OCC)(=O)C>[C:1]1([C:7]2([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 708171-Phenylcyclohexane-1-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 1985171-Phenylcyclohexanemethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-phenylcyclohexanecarboxylic acid (1.32 g) in tetrahydrofuran (30 mL) at 0° C. was slowly added 2 M LiAlH4 in tetrahydrofuran (6.46 mL). The resulting mixture was stirred at room temperature overnight and cooled to 0° C. Ice water was added to quench the reaction. The resulting mixture was diluted with ethyl acetate and washed with 1 N aqueous NaOH and water. The organic layer was dried over Na2SO4, filtered, and concentrated to provide the title compound.

Workup

  1. customat 0° C.
  2. temperaturecooled to 0° C
  3. customto quench
  4. customthe reaction
  5. washwashed with 1 N aqueous NaOH and water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b2f6d9693d0c4351927756002e2491e6
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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