Ethyl 4-oxocyclohexanecarboxylate → 4-Oxocyclohexanecarboxylic acid

HRID 1244672Notes

Reaction equation

HRID 1244672 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5])C>OS(O)(=O)=O>[O:12]=[C:9]1[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1

Participants

3

Reactant 1

HCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 1927304-Oxocyclohexanecarboxylic acidYield 102%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

20 mmol (3.4 g) of 4-oxocyclohexanecarboxylic acid ethyl ester is suspended in 40 ml of 2% H2SO4 and stirred for 2 hours at 90° C. Then, it is extracted 4 times with ethyl acetate, dried with Na2SO4, and solvent is removed. Recrystallization is carried out from ether/hexane and yields 2.9 g of white solid 3.

Workup

  1. extractionThen, it is extracted 4 times with ethyl acetate
  2. dry with materialdried with Na2SO4, and solvent
  3. customis removed
  4. customRecrystallization

Sources & evidence

ORD record
ord-a0c82ea094bd418e88857c673be9dc7b
Source dataset
uspto-grants-2006_10
Patent number
US07122570B2

Reaction notes

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