Ammonia acetate → 3,3,5-Trimethylcyclohexanone

HRID 268193

Reaction equation

HRID 268193 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.N>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 12432Ammonia acetateHCID 133983,3,5-TrimethylcyclohexanoneHCID 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 ammonia acetate (1.0 g.) were mixed, stored 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° 10.7 mm. of 3,3,5'-trimethyl-1,1'-peroxy-dicyclohexylamine (peroxide equivalent, 234; perchloric acid equivalent, 245; and residue (1.5 g.).

Workup

  1. distillationDistillation

Sources & evidence

ORD record
ord-e8663b9339e748698fc7f0e0479767fa
Source dataset
uspto-grants-1976_03
Patent number
US03947406

Linked notes

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