Ethylparaben → Ethyl 4-oxocyclohexanecarboxylate

HRID 323995Notes

Reaction equation

HRID 323995 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[Pd]>[CH:5]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4][CH2:3][C:2](=[O:1])[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 8434Ethylparaben

Product 1

HCID 317638Ethyl 4-oxocyclohexanecarboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 50 g of ethyl 4-hydroxybenzoate in 500 ml of toluene is hydrogenated at 2.5 bar and 110° C. in the presence of palladium on activated carbon. The reaction mixture is filtered and freed from water by azeotropic distillation. It is then treated with 10 g of pyridine sulfone and stirred at 50° C. for 1 hour. After filtration with basic alumina and removal of the solvent, 49.6 g (97% yield) of ethyl cyclohexan-4-onecarboxylate having a purity of 94.1% (GC) remain.

Workup

  1. filtrationThe reaction mixture is filtered
  2. distillationfreed from water by azeotropic distillation
  3. additionIt is then treated with 10 g of pyridine sulfone
  4. filtrationAfter filtration

Sources & evidence

ORD record
ord-c65f7c9a4d6f47ec95a1efca9fa06e67
Source dataset
uspto-grants-2001_04
Patent number
US06215028B1

Reaction notes

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