Diethyl Ether → 3-(1,3-Butadien-1-yl)-2,4,4-trimethyl-2-cyclohexen-1-one

HRID 1902386Notes

Reaction equation

HRID 1902386 reaction equation
[CH3:1][C:2]1[CH2:8][C:6](=O)[CH2:5][C:4]([CH3:10])([CH3:9])[C:3]=1/[CH:11]=[CH:12]/[CH:13](O)[CH3:14].C1(C)C=CC(S(O)(=O)=[O:23])=CC=1.CCOCC>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:8](=[O:23])[CH2:6][CH2:5][C:4]([CH3:10])([CH3:9])[C:3]=1[CH:11]=[CH:12][CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 91748029HCID 91748029, compound

Product 1

HCID 30200643-(1,3-Butadien-1-yl)-2,4,4-trimethyl-2-cyclohexen-1-oneYield 2,715%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 70 g of crude 3-oxo-β-ionol and 1.5 g of paratoluenesulphonic acid in 300 ml of toluene is stirred at reflux temperature for 40 minutes with simultaneous removal of the water formed by means of a water separator. The cooled mixture is treated with 300 ml of ether, the organic phase is washed three times with soda solution and three times with water, dried and concentrated. There are obtained 61 g of crude product which contains more than 90% of 2,4,4-trimethyl-3-(buta-1,3-diethyl)cyclohex-2-en-1-one according to gas-chromatographical analysis. Distillation of the crude product over a 15 cm column gives 45 g of olfactorily-good 2,4,4-trimethyl-3-(buta-1,3-dienyl)cyclohex-2-en-1-one of boiling point 74°-75° C./0.06 mm Hg.

Workup

  1. temperatureat reflux temperature for 40 minutes
  2. customwith simultaneous removal of the water
  3. customformed by means of a water separator
  4. washthe organic phase is washed three times with soda solution and three times with water
  5. customdried
  6. concentrationconcentrated
  7. customThere are obtained 61 g of crude product which
  8. distillationDistillation of the crude product over a 15 cm column

Sources & evidence

ORD record
ord-528f1a39a0c0415db993d66b00c2a866
Source dataset
uspto-grants-1982_12
Patent number
US04363331

Reaction notes

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