Hydrogen Peroxide → HCID 19876539, compound

HRID 1886566Notes

Reaction equation

HRID 1886566 reaction equation
ClC(C1C(C)CC(C)(C)C(=[O:18])C1)C1C=CC=CC=1.[Cl:19][C:20]1[CH:36]=[CH:35][C:23]([CH2:24][C:25]2[CH:30]([CH3:31])[CH2:29][C:28]([CH3:33])([CH3:32])[C:27](=[O:34])[CH:26]=2)=[CH:22][CH:21]=1.[OH-].[Na+].OO>CO>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][C:25]23[O:18][CH:26]2[C:27](=[O:34])[C:28]([CH3:33])([CH3:32])[CH2:29][CH:30]3[CH3:31])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 19771304HCID 19771304, compoundHCID 19771309HCID 19771309, compound

Product 1

HCID 19876539HCID 19876539, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

The 1-(chlorobenzyl)-4,4,6-trimethylcyclohexan-3-one (315 g, 1.2 mol) obtained in (b) above was added to methanol (1500 ml) and the mixture warmed to 40° C. to give a clear yellow solution. The solution was then cooled to 10° C. and aqueous sodium hydroxide (25 g in 112 ml water) was added over a period of 10 minutes. Whilst maintaining the temperature of the reaction mixture between 15° and 20° C., 30% (w/v) aqueous hydrogen peroxide (138 ml, 1.2 mol) was added over a period of 30 minutes and the mixture was then stirred overnight. A further 30 ml was then added and the mixture stirred for 21/2 hours. The reaction mixture was then concentrated under reduced pressure and diluted with water (2 liters) and diethyl ether (1.5 liters). The aqueous layer was then extracted with diethyl ether (2×0.5 liters), dried and the solvent flashed off to give 1-(4 -chlorobenzyl)-1,2-epoxy-4,4,6-trimethylcyclohexan-3-one as a crystalline white solid (271 g), m.pt. 58°-59° C.

Workup

  1. customto give a clear yellow solution
  2. temperatureThe solution was then cooled to 10° C.
  3. additionwas added over a period of 30 minutes
  4. additionA further 30 ml was then added
  5. stirringthe mixture stirred for 21/2 hours
  6. concentrationThe reaction mixture was then concentrated under reduced pressure
  7. additiondiluted with water (2 liters) and diethyl ether (1.5 liters)
  8. extractionThe aqueous layer was then extracted with diethyl ether (2×0.5 liters)
  9. customdried

Sources & evidence

ORD record
ord-7796e5fd81144ce08d6c903652365569
Source dataset
uspto-grants-1992_09
Patent number
US05151550

Reaction notes

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