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

HRID 2398706Notes

Reaction equation

HRID 2398706 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) bp 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-d92f74f1978a4c7bbf35e4c453bf3253
Source dataset
uspto-grants-1977_05
Patent number
US04025564

Reaction notes

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