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

HRID 1974214Notes

Reaction equation

HRID 1974214 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 inch 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 inch vacuum

Sources & evidence

ORD record
ord-7e5a5b28ea4845dda657d116fed47b92
Source dataset
uspto-grants-1976_12
Patent number
US04000198

Reaction notes

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