Ethanol → 2-Ethoxycyclohex-2-en-1-one

HRID 1455083Notes

Reaction equation

HRID 1455083 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.C[OH:17].[CH2:18]([OH:20])[CH3:19]>C1(C)C=CC=CC=1>[CH2:18]([O:20][C:6]1[C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH:5]=1)[CH3:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 21584188Chloroform methanol

Product 1

HCID 1215982-Ethoxycyclohex-2-en-1-oneYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 g (0.45 mol) of 1,2-dicyclohexandione were dissolved in a mixture of 1 L of toluene and 0.5 L of ethanol. 10 g of p-toluenesulfonic acid were added and the solution heated at reflux for 2 days. (TLC chloroform/methanol 6/1). The solvent was then evaporated, the residue redissolved with dichloromethane and washed with a saturated solution of NaHCO3. The organic layer was dried over Na2SO4 and concentrated. The crude was purified by chromatography on a silica gel column by eluting with a mixture of cyclohexane/ethyl acetate 98/2 (66% yield as an oil).

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 2 days
  3. customThe solvent was then evaporated
  4. dissolutionthe residue redissolved with dichloromethane
  5. washwashed with a saturated solution of NaHCO3
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude was purified by chromatography on a silica gel column
  9. washby eluting with a mixture of cyclohexane/ethyl acetate 98/2 (66% yield as an oil)

Sources & evidence

ORD record
ord-3207030e9d294bdbbf6b7f066bb5cf68
Source dataset
uspto-grants-2009_01
Patent number
US07482354B2

Reaction notes

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