4-Hydroxybenzoic Acid → Cyclohexanecarboxylic acid

HRID 845133Notes

Reaction equation

HRID 845133 reaction equation
O[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[H][H]>C(O)(C)C.[C].[Pd]>[CH2:2]1[CH2:10][CH2:9][CH:5]([C:6]([OH:8])=[O:7])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 7413Cyclohexanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

One mole of 4-hyroxybenzoic acid was reacted with two moles of hydrogen in the presence of 5% palladium-carbon catlyst. This reaction was carried out in isopropyl alcohol at a temperature of 130°-140° C. and a hydrogen pressure of 20-40 kg/cm2 (gauge). After the reaction mixture was filtered to recover the catalyst therefrom, the filtrate was distilled to recover the solvent. The resulting residue was recrystallized from a mixture of benzene and hexane to obtain cyclohexane-4-carboxylic acid. This product had a melting point of 67.0°-68.0° C.

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. customto recover the catalyst
  3. distillationthe filtrate was distilled
  4. customto recover the solvent
  5. customThe resulting residue was recrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-3ea57813eb404e09bf73eb146cfcfc2a
Source dataset
uspto-grants-1988_07
Patent number
US04755616

Reaction notes

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