Sodium Hydroxide → Dihydroandrostenedione

HRID 467452

Reaction equation

HRID 467452 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH-].[Na+]>CC(C)=O>[CH3:13][C@:12]12[CH2:14][CH2:15][C@H:16]3[C@@H:7]([CH2:6][CH2:5][C@@H:4]4[C@:17]3([CH3:20])[CH2:18][CH2:19][C:2](=[O:1])[CH2:3]4)[C@@H:8]1[CH2:9][CH2:10][C:11]2=[O:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 441302EpiandrosteroneHCID 131709961Jones' reagent

Product 1

HCID 222865DihydroandrostenedioneYield 95.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the mixture of 6 (5 g, 17.2 mmol) and 75 ml acetone at room temperature 1.5 ml of Jones reagent (CrO3, H2SO4, H2O) was added by drops. After the reaction was completed, NaOH was added, liquid phase was separated and then 90 ml water was added. The resulting precipitate was filtered off to afford product 7 (4.72 g, 94%). M.p. 134-137° C.

Workup

  1. additionwas added by drops
  2. customliquid phase was separated
  3. addition90 ml water was added
  4. filtrationThe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-08e7bcdbab2549c384510081d8f10672
Source dataset
uspto-grants-2014_01
Patent number
US08623849B2

Linked notes

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