4-Hydroxybenzoic Acid → 4-Hydroxycyclohexanecarboxylic acid

HRID 597116Notes

Reaction equation

HRID 597116 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+]>[Pt]=O.C(O)C>[OH:1][CH: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 14797Potassium Hydroxide

Product 1

HCID 1511384-Hydroxycyclohexanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 42 parts of p-hydroxybenzoic acid, 2 parts of platinum oxide, 1 part of 10% aqueous potassium hydroxide and 150 parts by volume of ethanol was charged to a hydrogenation flask. The mixture was hydrogenated at 50 psi for 32 hours. The reaction mixture was filtered and the solvent evaporated. The solid product was slurried in 500 parts by volume of hot cyclohexane to remove cyclohexane carboxylic acid, filtered, and the solids recrystallized from 100 parts of water. The solid, unreacted p-hydroxybenzoic acid, was filtered off and the water evaporated yielding 16 parts of 4-hydroxycyclohexane carboxylic acid having a melting point of 110°-130° C.

Workup

  1. additionwas charged to a hydrogenation flask
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent evaporated
  4. customto remove cyclohexane carboxylic acid
  5. filtrationfiltered
  6. customthe solids recrystallized from 100 parts of water
  7. filtrationThe solid, unreacted p-hydroxybenzoic acid, was filtered off
  8. customthe water evaporated

Sources & evidence

ORD record
ord-840576af1f5e4f3d97cfcc0f61f61e7f
Source dataset
uspto-grants-1977_03
Patent number
US04013582

Reaction notes

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