Potassium Hydroxide → 4-{[1,1'-Biphenyl]-4-yl}butanoic acid

HRID 2352573Notes

Reaction equation

HRID 2352573 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C(O)C.O>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19843451Ethyl 4-([1,1'-biphenyl]-4-yl)butanoate

Product 1

HCID 111392304-{[1,1'-Biphenyl]-4-yl}butanoic acidYield 97.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of ethyl 4-(4-phenylphenyl)butanoate (21.0 g) and potassium hydroxide (9.65 g) in ethanol (50 ml) and water (50 ml) was heated under reflux for 2 hours. The resulting mixture was allowed to cool, diluted with water (150 ml), washed with ether (x2), acidified with concentrated hydrochloric acid, and extracted with ether. The extracts were washed with water, dried and concentrated to give crude 4-(4-phenylphenyl)butanoic acid [(3), 18.28 g] as a white solid, m.p. 111°-113° C. (D. H. Hey and R. Wilkinson, J. Chem. Soc., 1940, 1030, give a m.p. of 118°-119° C. for this acid).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureto cool
  3. washwashed with ether (x2)
  4. extractionextracted with ether
  5. washThe extracts were washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c681ead0eda746aa8570a9e5697af6f5
Source dataset
uspto-grants-1989_10
Patent number
US04877811

Reaction notes

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