Potassium Hydroxide → β-Cyclohexylbenzeneethanol

HRID 902611Notes

Reaction equation

HRID 902611 reaction equation
C[O:2][C:3](=O)[CH:4]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+]>C1COCC1>[CH:11]1([CH:4]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:3][OH:2])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 13096512HCID 13096512, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3610110β-CyclohexylbenzeneethanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-cyclohexyl-2-phenyl-acetic acid methyl ester (2.2 g, 0.0094 mole) in THF (20 mL) was added 19 mL of a lithium aluminum hydride solution (1.0 M in THF) at 0° C. The reaction mixture was stirred overnight and 10% KOH (8 mL) was added. The mixture was filtered, and then washed with ether. Ether (60 mL) was added to the filtrate and the ethereal solution was washed with water (50 mL). The ether layer was dried over sodium sulfate, filtered, and concentrated to give 1.86 g (97% yield) of the title compound as an oil. 1H-NMR (400 MHz, CDCl3) δ 7.37-7.15 (m, 5H), 3.97 (t, 1H, J=6.0 Hz), 3.86 (t, 1H, J=9.0 Hz), 2.59 (q, 1H, J=4.0 Hz), 1.96-1.03 (m, 11H). The primary alcohol was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with ether
  3. additionEther (60 mL) was added to the filtrate
  4. washthe ethereal solution was washed with water (50 mL)
  5. dry with materialThe ether layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2ff037a151884bccaf8ffcff196ae74c
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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