Cyclopentanone → Cyclopentanone

HRID 268190

Reaction equation

HRID 268190 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+].N[C:13]1([O:22]O)[CH2:18][CH:17]([CH3:19])[CH2:16][C:15]([CH3:21])([CH3:20])[CH2:14]1>C(O)C>[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][CH:17]1[CH2:16][C:15]([CH3:21])([CH3:20])[CH2:14][C:13](=[O:22])[CH2:18]1

Participants

6

Reactant 3

HCID 8452CyclopentanoneHCID 517165Ammonium AcetateHCID 215101831-Amino-3,3,5-trimethylcyclohexyl hydroperoxide

Product 2

HCID 8452CyclopentanoneHCID 133983,3,5-Trimethylcyclohexanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of cyclopentanone (33.8 g.) and ethanol (100 c.c.) containing ammonium acetate (3.2 g.) and kept at or below 0°, was added 1-amino-3,3,5-trimethylcyclohexyl hydroperoxide (44.6 g., 68% pure). After storing at 0°C overnight the reaction mixture was worked up as in the previous Examples to give unreacted cyclopentanone and dihydroisophorone together with a fraction (20.0 g.) b.p. 82° - 86°/0.5 mm. This last fraction was redistilled to give: material b.p. 74° - 76°C/0.3 mm.Hg., peroxide equivalent 202, shown by mass spectroscopy to be a mixture of the peroxide ##SPC28##

Workup

  1. custombelow 0°

Sources & evidence

ORD record
ord-c2312b3c7a954db9ac998e9403e51f27
Source dataset
uspto-grants-1976_03
Patent number
US03947406

Linked notes

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