4-Cyclohexylbenzoic acid → (4-Cyclohexylphenyl)methanol

HRID 2180764Notes

Reaction equation

HRID 2180764 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 4-cyclohexylbenzoic acid (Aldrich; 1 molar eq.) in toluene was added diiso-butylaluminum 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 we're 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 we're 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-ea34b1c61dc54e21ba74a3a74386a654
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

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