Acetic Acid → (1,1'-Bi(cyclohexane))-4-carboxylic acid

HRID 477962Notes

Reaction equation

HRID 477962 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][CH:2]=1.C(O)(=O)C>C(O)C.[Pt]=O>[CH:1]1([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:2][CH2:3][CH:4]([C:7]([OH:9])=[O:8])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66724(1,1'-Biphenyl)-4-carboxylic acid

Product 1

HCID 3062287(1,1'-Bi(cyclohexane))-4-carboxylic acidYield 99.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of biphenyl-4-carboxylic acid (9.9 g, 50 mmol) in 500 ml of ethanol and 150 ml of glacial acetic acid containing 1.0 g of platinum oxide was hydrogenated overnight at 40 psi. Upon filtering the solution and concentrating the filtrate under reduced pressure, 10.5 g of bicyclohexyl-4-carboxylic acid was obtained as a white solid (m.p. 122°-125° C.).

Workup

  1. filtrationUpon filtering the solution
  2. concentrationconcentrating the filtrate under reduced pressure

Sources & evidence

ORD record
ord-5c7754857a03410781bccfdb46480e02
Source dataset
uspto-grants-1989_12
Patent number
US04889874

Reaction notes

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