Hydrogen Peroxide → HCID 86734051, compound

HRID 1287369Notes

Reaction equation

HRID 1287369 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][CH2:3]2.[OH:21]O.[OH-].[Na+]>CO.O>[O:21]1[C:10]23[C@:15]([CH3:16])([CH2:14][CH2:13][C:12](=[O:20])[C@H:11]12)[C@@H:17]1[C@H:7]([C@H:6]2[C@@:2]([CH2:19][CH2:18]1)([CH3:1])[CH2:3][CH2:4][CH2:5]2)[CH2:8][CH2:9]3

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25029417-Deoxytestosterone

Product 1

HCID 86734051HCID 86734051, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
3 °C

Procedure

4-Androstene-3-one (4.3g) is dissolved in 300ml of methanol and cooled to 3° C in an ice-water bath. To the cooled mixture is added 20ml of 30% hydrogen peroxide and 26ml of 4N sodium hydroxide solution simultaneously from 2 dropping funnels. The addition is carried out in a nitrogen atmosphere with stirring. The mixture is allowed to warm to room temperature and stirring is continued for an additional hour. The mixture is diluted with 4 liters of water and extracted with methylene chloride. The organic layer is dried over sodium sulfate and concentrated to yield 3.0g of the title compound.

Workup

  1. additionThe addition
  2. temperatureto warm to room temperature
  3. stirringstirring
  4. waitis continued for an additional hour
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e05b3f3e80344ba5abe5c7874ea840db
Source dataset
uspto-grants-1976_10
Patent number
US03984474

Reaction notes

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