4-Cyclohexylbenzoic acid → (4-Cyclohexylphenyl)methanol

HRID 636153

Reaction equation

HRID 636153 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 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-872ff1cb73e24d86a52403fbc8262162
Source dataset
uspto-grants-2001_02
Patent number
US06191166B1

Linked notes

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