Benzene → 2-Cyclohexen-1-one, 2,6,6-trimethyl-3-(2-methylpropoxy)-

HRID 442404Notes

Reaction equation

HRID 442404 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([CH3:10])([CH3:9])[C:3]1=[O:11].C1C=CC=CC=1.[CH2:18](O)[CH:19]([CH3:21])[CH3:20].CC1C=CC(S(O)(=O)=O)=CC=1>O>[CH3:1][C:2]1[C:3](=[O:11])[C:4]([CH3:10])([CH3:9])[CH2:5][CH2:6][C:7]=1[O:8][CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 6560IsobutanolHCID 70585111HCID 70585111, compound

Product 1

HCID 109217652-Cyclohexen-1-one, 2,6,6-trimethyl-3-(2-methylpropoxy)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound 2,6,6-trimethylcyclohexen-1,3-dione (43.6 g) was added to a mixture of benzene (250 ml), isobutanol (50 ml) and PTSA (500 mg) and heated under reflux for 3 hr in conjunction with a Dean and Stark water separator. The reaction was then cooled to room tmperature, washed with aqueous sodium carbonate solution and brine and taken to dryness in vacuo. Distillation of residue through a 6 inch vacuum jacketed vigreaux column yielded pure 2,6,6-trimethyl-3-isobutoxycyclohex-2-en-1 one (54.6 g) b p 104°-107°.

Workup

  1. temperatureheated
  2. temperatureThe reaction was then cooled to room tmperature
  3. washwashed with aqueous sodium carbonate solution and brine
  4. distillationDistillation of residue through a 6 inch vacuum

Sources & evidence

ORD record
ord-c2ae4c8be01c44ea893f691f36e91e81
Source dataset
uspto-grants-1977_08
Patent number
US04045476

Reaction notes

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