Acetophenone → Acetophenone

HRID 268189

Reaction equation

HRID 268189 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C([O-])(=O)C.[NH4+].N[C:16]1([O:25]O)[CH2:21][CH:20]([CH3:22])[CH2:19][C:18]([CH3:24])([CH3:23])[CH2:17]1>C(O)C>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:22][CH:20]1[CH2:19][C:18]([CH3:24])([CH3:23])[CH2:17][C:16](=[O:25])[CH2:21]1

Participants

6

Reactant 3

HCID 7410AcetophenoneHCID 517165Ammonium AcetateHCID 215101831-Amino-3,3,5-trimethylcyclohexyl hydroperoxide

Product 2

HCID 7410AcetophenoneHCID 133983,3,5-Trimethylcyclohexanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of acetophenone (24.3 g.) in ethanol (50 c.c.) containing ammonium acetate (1.6 g.) and kept at or below 0°C, was added 1-amino-3,3,5-trimethylcyclohexyl hydroperoxide (17.3 g.; pure). The solution was kept at 0°C overnight and then worked up as in the previous Examples to give unreacted acetophenone and dihydroisophorone, and a fraction (4.8 g.), b.p. 126° - 130°/0.5 mm. with a peroxide equivalent of 407, shown by mass spectroscopy to contain the peroxide ##SPC26##

Workup

  1. custombelow 0°C

Sources & evidence

ORD record
ord-b81d25f4e0e24e97893e6f0450e86cf8
Source dataset
uspto-grants-1976_03
Patent number
US03947406

Linked notes

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