Hydrogen Peroxide → Testosterone

HRID 1287367Notes

Reaction equation

HRID 1287367 reaction equation
[OH-:1].[Na+].OO.[CH3:5][C@@:6]12[C@@H:14]([OH:15])[CH2:13][CH2:12][C@H:11]1[C@@H:10]1[CH2:16][CH2:17][C:18]3[C@@:24]([CH3:25])([C@H:9]1[CH2:8][CH2:7]2)[CH2:23][CH2:22][C:20](=[O:21])[CH:19]=3>CO>[CH3:5][C@@:6]12[C@@H:14]([OH:15])[CH2:13][CH2:12][C@H:11]1[C@@H:10]1[CH2:16][CH2:17][C:18]3[C@@:24]([CH3:25])([C@H:9]1[CH2:8][CH2:7]2)[CH2:23][CH2:22][C:20](=[O:21])[CH:19]=3.[O:1]1[C:18]23[C@:24]([CH3:25])([CH2:23][CH2:22][C:20](=[O:21])[C@H:19]12)[C@@H:9]1[C@H:10]([C@H:11]2[C@@:6]([CH2:7][CH2:8]1)([CH3:5])[C@@H:14]([OH:15])[CH2:13][CH2:12]2)[CH2:16][CH2:17]3

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 6013TestosteroneHCID 14798Sodium Hydroxide

Product 2

HCID 6013TestosteroneHCID 86734049HCID 86734049, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
3 °C

Procedure

A solution of 33g of testosterone in 1500ml of methanol is prepared and cooled in an ice bath to 3°C. Over an hour period, 191ml of 4N sodium hydroxide and 143ml of 30% hydrogen peroxide are added simultaneously. The mixture is stirred at 3° C for an additional 3 hours after which thin layer chromatography shows that the testosterone has been completely consumed. The mixture is poured into 20 gallons of ice water contain 3 pounds of salt and the title epoxide crysallizes. The crystalline material is filtered with suction and the residue is washed with water on the filter and dried to yield 10.5g of the title compound.

Workup

  1. customhas been completely consumed
  2. additionThe mixture is poured into 20 gallons of ice water
  3. filtrationThe crystalline material is filtered with suction
  4. washthe residue is washed with water on the
  5. filtrationfilter
  6. customdried

Sources & evidence

ORD record
ord-fcf6f6a9d8b04038b56dae7cbc354509
Source dataset
uspto-grants-1976_10
Patent number
US03984474

Reaction notes

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