Ethyl Acrylate → 2-Acetyl-2-[2-(ethoxycarbonyl)ethyl]cyclohexanone

HRID 374343Notes

Reaction equation

HRID 374343 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([C:4]1([CH2:19][CH2:18][C:17]([O:21][CH2:22][CH3:23])=[O:20])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 11430Potassium CarbonateHCID 134002-Acetylcyclohexanone

Product 1

HCID 190674842-Acetyl-2-[2-(ethoxycarbonyl)ethyl]cyclohexanoneYield 97%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-acetylcyclohexanone (25 g, 0.18 mol), potassium carbonate (29.5 g, 0.21 mol) and benzyltriethylammonium chloride (0.8 g, 0.0035 mol) in toluene (70 ml) was added ethyl acrylate (29 ml, 27 g, 0.27 mol) at room temperature. The mixture was heated at 40° C. for 20 hours, filtered and partitioned between distilled water (200 ml) and toluene (200 ml). The organic layer was dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the title compound as a brown oil, (41.7 g, 97%) .

Workup

  1. filtrationfiltered
  2. custompartitioned
  3. distillationbetween distilled water (200 ml) and toluene (200 ml)
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01c5b4230fd5493da95733cce2825d6a
Source dataset
uspto-grants-1992_11
Patent number
US05166406

Reaction notes

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