Sulfuric Acid → 2-Cyclohexen-1-one, 4,4-dimethyl-

HRID 1018793Notes

Reaction equation

HRID 1018793 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7](=[O:10])[CH:8]=[CH2:9].[CH3:11][CH:12]([CH3:15])[CH:13]=O>C1C=CC=CC=1>[CH3:11][C:12]1([CH3:15])[CH2:13][CH2:6][C:7](=[O:10])[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6561IsobutyraldehydeHCID 6570Methyl vinyl ketone

Product 1

HCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1 ml of concentrated sulphuric acid is added at room temperature to 81 ml of but-3-en-2-one and 88 ml of 2-methylpropionaldehyde in 450 ml of benzene, after which the reaction mixture is refluxed for 13 hours to remove the water by azeotropic entrainment. After cooling to room temperature, the reaction mixture is washed with saturated aqueous sodium bicarbonate solution and then with water. The organic phase is dried over magnesium sulphate and the solvents are evaporated off under reduced pressure. After distillation, 31.1 g of the expected compound are isolated; b.p.=78° C. (at a pressure of 22 mbar).

Workup

  1. temperatureafter which the reaction mixture is refluxed for 13 hours
  2. customto remove the water by azeotropic entrainment
  3. washthe reaction mixture is washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customthe solvents are evaporated off under reduced pressure
  6. distillationAfter distillation, 31.1 g of the expected compound
  7. customare isolated

Sources & evidence

ORD record
ord-25348c1fa2ca46b69bf34e94192f59c1
Source dataset
uspto-grants-2002_11
Patent number
US06482986B1

Reaction notes

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