Ethanol → Ethyl 3-oxocyclohexanecarboxylate

HRID 1526498Notes

Reaction equation

HRID 1526498 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([OH:10])=[O:9])[CH2:3]1.[CH2:11](O)[CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 27602523-Oxocyclohexane-1-carboxylic acid

Product 1

HCID 118096Ethyl 3-oxocyclohexanecarboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-oxocyclohexane-1-carboxylic acid (8.7 g, 61.20 mmol, 1.00 equiv) and ethanol (21 mL) in toluene (150 mL) was added p-toluenesulfonic acid (250 mg) at room temperature and the resulting solution was heated to reflux overnight in presence of a Dean-Stark. After completion, the resulting mixture was concentrated under vacuum and the residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4) to give the desired ethyl 3-oxocyclohexane-1-carboxylate (7.5 g, 72%) as white oil.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux overnight in presence of a Dean-Stark
  3. concentrationAfter completion, the resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-19f6854a21fe48d5bdb8bd6b82444b25
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

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