Acetone → 3,3,5-Trimethylcyclohexanone

HRID 1576887Notes

Reaction equation

HRID 1576887 reaction equation
CC(C)=O.N[C:6]1([O:15]O)[CH2:11][CH:10]([CH3:12])[CH2:9][C:8]([CH3:14])([CH3:13])[CH2:7]1.S([O-])([O-])(=O)=O.[Mg+2]>C(O)C>[CH3:12][CH:10]1[CH2:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6](=[O:15])[CH2:11]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 215101831-Amino-3,3,5-trimethylcyclohexyl hydroperoxide

Product 1

HCID 133983,3,5-Trimethylcyclohexanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetone (11.6 g.) in ethanol (50 c.c.) was stirred at below 0°C and 1-amino-3,3,5-trimethylcyclohexyl hydroperoxide (17.3 g; 80% pure) added. After stirring for ca. 1 hour the solid had dissolved. To the solution was added magnesium sulphate and it was stored at 0°C overnight. Filtration and distillation gave acetone and dihydroisophorone (probably containing some symmetrical amino-peroxide ##STR19## and a product (2.2 g.), b.p. 75° - 78°C/ 1.0 mm, had a peroxide equivalent 239.4 and gave N, 6.3% an elemental analysis.

Workup

  1. dissolutionhad dissolved
  2. waitwas stored at 0°C overnight
  3. filtrationFiltration and distillation

Sources & evidence

ORD record
ord-91d3060fa49e4b9b85302df37d6168ca
Source dataset
uspto-grants-1976_09
Patent number
US03983142

Reaction notes

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