Phosphoric Acid → 9-Dehydroandrostenedione

HRID 1087679Notes

Reaction equation

HRID 1087679 reaction equation
O[C@:2]12[CH2:19][CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:20])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=1.P(=O)(O)(O)O>O>[CH3:17][C@:16]12[CH2:18][CH:19]=[C:2]3[C@@H:11]([CH2:10][CH2:9][C:8]4[C@:3]3([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=4)[C@@H:12]1[CH2:13][CH2:14][C:15]2=[O:20]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 104250179alpha-Hydroxyandrost-4-ene-3,17-dione

Product 1

HCID 2395959-Dehydroandrostenedione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9α-Hydroxyandrostenedione (9.06 g.) is added to phosphoric acid (85%, 25 ml.) and stirred at 45°-55° for 24 hours. Water (75 ml.) is added, the mixture stirred for 2 hours and the solids are collected by filtration. The solids are washed with water (200 ml.) and air-dried to give androsta-4,9(11)-diene-3,17-dione, 8.11 g., (95.1% chemical yield); m.p. 193°-195°.

Workup

  1. stirringthe mixture stirred for 2 hours
  2. filtrationthe solids are collected by filtration
  3. washThe solids are washed with water (200 ml.)
  4. customair-dried

Sources & evidence

ORD record
ord-c004e900d17244aca4f89d8fc4faef58
Source dataset
uspto-grants-1990_10
Patent number
USRE033364

Reaction notes

Loading…