Acetone → Ethyl 4-oxocyclohexanecarboxylate

HRID 1359411Notes

Reaction equation

HRID 1359411 reaction equation
CC(C)=O.[OH:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][CH2:7]1.CC(O)C>O>[CH2:15]([O:14][C:12]([CH:9]1[CH2:10][CH2:11][C:6](=[O:5])[CH2:7][CH2:8]1)=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 180AcetoneHCID 3776IsopropanolHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Product 1

HCID 317638Ethyl 4-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

120 ml of a Jone's reagent was added dropwise into a solution of 800 ml of acetone containing 81.1 g of ethyl 4-hydroxycyclohexane carboxylate over 30 minutes in an ice bath. After stirring at the same temperature for 20 minutes, 2-propanol was added thereto. The reaction solution was poured into water, followed by extracting with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and the solvent was removed, to give 80.0 g of the target compound.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-fde7ec98394547ad9715001c0cac7ce7
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

Loading…