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

HRID 262334Notes

Reaction equation

HRID 262334 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 temperature, washed with aqueous sodium carbonate solution and brine and taken to dryness "in vacuo". Distillation of residue through a 6" 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. washwashed with aqueous sodium carbonate solution and brine
  3. distillationDistillation of residue through a 6" vacuum

Sources & evidence

ORD record
ord-9619adc1868045b49f48b44df9fd8895
Source dataset
uspto-grants-1979_05
Patent number
US04153805

Reaction notes

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