Phenylacetaldehyde → 2-Cyclohexen-1-one, 4-phenyl-

HRID 1243845Notes

Reaction equation

HRID 1243845 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10]([C:12]([CH3:14])=[O:13])=[CH2:11].S(=O)(=O)(O)O.C1(C)C=CC=CC=1>C(OCC)(=O)C>[C:1]1([CH:7]2[CH2:8][CH2:14][C:12](=[O:13])[CH:10]=[CH:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 1118Sulfuric AcidHCID 1140TolueneHCID 6570Methyl vinyl ketone

Product 1

HCID 110628762-Cyclohexen-1-one, 4-phenyl-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 19.5 cm3 of phenylacetaldehyde, 16.7 cm3 of methyl vinyl ketone, 0.17 cm3 of 36% sulphuric acid and 85 cm3 of toluene is heated for 1 hour at a temperature in the region of the reflux temperature. After cooling to a temperature in the region of 20° C., 50 cm3 of ethyl acetate are added to the reaction mixture. The resulting mixture is washed with 100 cm3 of saturated aqueous sodium bicarbonate solution and then dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. The residue is purified by flash chromatography on a column of silica [eluent: cyclohexane/ethyl acetate (90/10)] to give 4.7 g of 4-phenylcyclohex-2-enone in the form of a yellow oil, the characteristics of which are as follows:

Workup

  1. temperatureis heated for 1 hour at a temperature in the region of the reflux temperature
  2. additionare added to the reaction mixture
  3. washThe resulting mixture is washed with 100 cm3 of saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue is purified by flash chromatography on a column of silica [eluent: cyclohexane/ethyl acetate (90/10)]

Sources & evidence

ORD record
ord-bd23c2dc667c41e0ab460b42affb2416
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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