4-Cyclohexylbenzoic acid → (4-Cyclohexylphenyl)methanol

HRID 322702Notes

Reaction equation

HRID 322702 reaction equation
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][OH:12])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 883374-Cyclohexylbenzoic acidHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 22492024(4-Cyclohexylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4cyclohexylbenzoic acid (Aldrich; 1 molar eq.) in toluene was added diisobutylaluminum hydride (Aldrich; 1 M in toluene; 4 molar eq.) over a 2 hour period. After addition was complete, the reaction was heated to 60° C. for 1 hour. The reaction was cooled to 5° C. and quenched with saturated aqueous ammonium chloride. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organics were filtered to remove salts and concentrated.

Workup

  1. additionAfter addition
  2. temperatureThe reaction was cooled to 5° C.
  3. customquenched with saturated aqueous ammonium chloride
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with ethyl acetate
  6. filtrationThe combined organics were filtered
  7. customto remove salts
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1ae4a04e146846a4ab1d12d37e57395c
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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