Water → HCID 228327, compound

HRID 1415725Notes

Reaction equation

HRID 1415725 reaction equation
[CH3:1][Al](C)C.[C:5](=[C:8]1[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][C:9]1=[O:15])([CH3:7])[CH3:6].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:5]([CH:8]1[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][C:9]1=[O:15])([CH3:1])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 6988PulegoneHCID 16682925Trimethylaluminum

Product 1

HCID 228327HCID 228327, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
25 °C

Procedure

28.5 ml (33 mmol) of trimethylaluminum as 10% solution in toluene is instilled in 4.56 g (30 mmol) of 2-isopropylidene-5-methyl-cyclohexan-1-one (pulegone) and 214.5 mg (1.5 mmol) of CuBr in 30 ml of ethyl acetate. The reaction solution is stirred for 1 more hour at 25° C. For hydrolysis, 2 ml of water is carefully added and stirred for 15 more minutes. The inorganic solid is suctioned off, rewashed with ethyl acetate and the solution is concentrated by evaporation in a vacuum. Distillation of the crude product at 120° C./6 torr yields 3.4 g of 2-tert-butyl-5-methyl-cyclohexanone (70% of theory) as a mixture of isomers.

Workup

  1. additionis carefully added
  2. stirringstirred for 15 more minutes
  3. concentrationthe solution is concentrated by evaporation in a vacuum
  4. distillationDistillation of the crude product at 120° C./6 torr

Sources & evidence

ORD record
ord-068c91c5f7ec4164a6b28906db4574e9
Source dataset
uspto-grants-1999_06
Patent number
US05908945

Reaction notes

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