Water → HCID 228327, compound

HRID 1415859Notes

Reaction equation

HRID 1415859 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 AcetateSolvent

Conditions

Temperature
25 °C

Procedure

28.5 ml (33 mmol) of trimethyl aluminum as 10% solution in toluene is instilled in 4.56 g (30 mmol) of 2-isopropylidene-5-methyl-cyclohexan-1-one (pulegon) and 214.5 mg (1.5 mmol) of CuBr in 30 ml of ethyl acetate. The reaction solution is stirred 1 hour more at 25° C. 2 ml of water is carefully added for hydrolysis and stirred for 15 minutes more. The inorganic solid is suctioned off, washed again 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 isomer mixture.

Workup

  1. stirringstirred for 15 minutes more
  2. washwashed again with ethyl acetate
  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-a07f207bd1ca44b29ba763f4866d37d5
Source dataset
uspto-grants-1999_06
Patent number
US05908944

Reaction notes

Loading…