3,3,5-Trimethylcyclohexanone → 3,3,5-Trimethylcyclohexanone

HRID 1576883Notes

Reaction equation

HRID 1576883 reaction equation
N[C:2]1([O:8]O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:10][CH:11]1[CH2:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:13](=[O:14])[CH2:12]1.C([O-])(=O)C.[NH4+]>CO>[C:2]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:10][CH:11]1[CH2:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:13](=[O:14])[CH2:12]1

Participants

6

Reactant 3

HCID 133983,3,5-TrimethylcyclohexanoneHCID 517165Ammonium AcetateHCID 193800581-Aminocyclohexyl hydroperoxide

Product 2

HCID 7967CyclohexanoneHCID 133983,3,5-TrimethylcyclohexanoneYield 64.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Aminocyclohexyl hydroperoxide (13.1 g), dihydroisophorone (14 g), methanol (25 cc.) and ammonium acetate (1.0 g) were mixed, store at 0°C overnight and worked up as in the previous example. Distillation gave cyclohexanone and dihydroisophorone (9.0 g), an intermediate fraction (3.2 g), b.p. below 100°C/0.7 mm,Hg., a fraction (8.1 g), b.p. 110°-114°/0.7 mm of 3,3,5'-trimethyl-1,1'-peroxy-dicyclohexylamine (peroxide equivalent, 234; perchloric acid equivalent, 245; and residue (1.5 g). The process may be carried out in the liquid or gas phase, but is preferably carried out in the gas phase as the liquid phase reaction tends to give a complex mixture of products of which only part are the desired derivatives of 1,12-dodecanedioic acid. The elevated temperature to which the 1,1'-peroxydicyclohexylamine is heated is suitably in the range 300°C to 600°C, and preferably from 400°C to 600°C. If the reaction is to be carried out in the gas phase it is preferred to use reduced pressures. Suitable pressures are of the order of 10 to 250 mm Hg.

Workup

  1. customat 0°C
  2. customovernight
  3. distillationDistillation

Sources & evidence

ORD record
ord-3389b9ed20c548819fcc78d1a5586d37
Source dataset
uspto-grants-1976_09
Patent number
US03983142

Reaction notes

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