Ethanol → HCID 19771308, compound

HRID 1886564Notes

Reaction equation

HRID 1886564 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9](=[O:15])[CH:8]=2)=[CH:4][CH:3]=1.C([OH:20])C.[OH-].[Na+].OO>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]23[O:20][CH:8]2[C:9](=[O:15])[C:10]([CH3:14])([CH3:13])[CH2:11][CH2:12]3)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 197713053-[(4-Chlorophenyl)methyl]-6,6-dimethylcyclohex-2-en-1-one

Product 1

HCID 19771308HCID 19771308, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

1726 g (6.945 mol) crude 1-(4-chlorobenzyl)-4,4-dimethylcyclohex-1-en-3-one obtained as described in (b) above and ethanol (8630 ml) were charged into a 20 liter reactor and warmed to 40° C. to give a clear pale orange solution. The reaction mixture was then cooled to 18° C. and 20% (w/v) sodium hydroxide (650 ml) was added slowly with cooling (ice/water) to maintain this temperature. Keeping the reaction mixture at a temperature between 11° and 20° C., 30% (w/v) aqueous hydrogen peroxide (794 ml, 7 mol) was added over a period of 1 hour and the mixture was then stirred overnight. Water (16 liters) was then added with ice cooling and the reaction mixture stirred for 15 minutes. Centrifugation followed by washing with water (4×21/2 liters) yielded an off-white solid which was then air dried to give 1634 g 1-(4-chlorobenzyl)-1,2-epoxy-4,4-dimethylcyclohexan-3-one, m.pt. 69°-70° C.

Workup

  1. additionwere charged into a 20 liter reactor
  2. customto give a clear pale orange solution
  3. temperatureThe reaction mixture was then cooled to 18° C.
  4. temperatureto maintain this temperature
  5. additionwas added over a period of 1 hour
  6. stirringthe reaction mixture stirred for 15 minutes
  7. washby washing with water (4×21/2 liters)
  8. customyielded an off-white solid which
  9. customair dried

Sources & evidence

ORD record
ord-43f55b6dd1f64aaa9c428c42599c9522
Source dataset
uspto-grants-1992_09
Patent number
US05151550

Reaction notes

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