Hydrogen Peroxide → HCID 12137343, compound

HRID 24296Notes

Reaction equation

HRID 24296 reaction equation
[Cl:1]/[CH:2]=[C:3]1/[C@:4]2([CH2:20][CH2:19][C@H:18]3[C@@H:9]([CH2:10][CH2:11][C:12]4[C@@H:17]3[CH2:16][CH2:15][C:14](=[O:21])[CH:13]=4)[C@@H:6]2[CH2:7][CH2:8]/1)[CH3:5].[OH:22]O.[OH-].[Na+]>CO.C(Cl)Cl>[Cl:1]/[CH:2]=[C:3]1/[C@:4]2([CH2:20][CH2:19][C@H:18]3[C@@H:9]([CH2:10][CH2:11][C:12]45[O:22][CH:13]4[C:14](=[O:21])[CH2:15][CH2:16][C@@H:17]53)[C@@H:6]2[CH2:7][CH2:8]/1)[CH3:5]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12137342HCID 12137342, compound

Product 1

HCID 12137343HCID 12137343, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3.93 mmol (1.2 9) of E-17-chloromethylen-estr-4-en-3-one is dissolved in a mixture of 12 ml of methanol and 10 ml of methylene chloride under a cover gas (argon) and cooled to 0° C. 9.2 mmol (0.94 ml) of hydrogen peroxide (30%) and 1.65 mmol (0.4 ml) of sodium hydroxide solution (c=4 mol/l) are added in drops in succession to the cooled solution while being stirred. After dropwise addition is completed, the temperature is slowly increased to room temperature. After about 1.5 hours of reaction time, the mixture is added to ice water and extracted with methylene chloride. The combined extracts are dried on sodium sulfate and concentrated by evaporation. 1.1 g of a white, sticky foam is obtained.

Workup

  1. additionAfter dropwise addition
  2. temperaturethe temperature is slowly increased to room temperature
  3. customAfter about 1.5 hours of reaction time
  4. extractionextracted with methylene chloride
  5. customThe combined extracts are dried on sodium sulfate
  6. concentrationconcentrated by evaporation
  7. custom1.1 g of a white, sticky foam is obtained

Sources & evidence

ORD record
ord-218db3192f18403dbcaa4cf8b0ca5fdc
Source dataset
uspto-grants-2005_02
Patent number
US06855836B2

Reaction notes

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