Hydrogen Peroxide → 2-Hydroxy-estradiol

HRID 1598938Notes

Reaction equation

HRID 1598938 reaction equation
OO.[OH-].[Na+].CC([O:8][C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][C@@H:16]3[C:25]4[C:20](=[CH:21][C:22]([OH:27])=[C:23]([OH:26])[CH:24]=4)[CH2:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)=O>>[CH3:28][C@@:13]12[C@@H:9]([OH:8])[CH2:10][CH2:11][C@H:12]1[C@H:17]1[C@@H:16]([C:25]3[CH:24]=[C:23]([OH:26])[C:22]([OH:27])=[CH:21][C:20]=3[CH2:19][CH2:18]1)[CH2:15][CH2:14]2

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 1855442-Hydroxyestradiol 17-acetate

Product 1

HCID 2473042-Hydroxy-estradiolYield 77%

Procedure

The following section describes the process for the manufacture of catechol estrogen glycosides from estradiol as starting material. The first step is that estradiol was reacted with acetic anhydride in pyridine at room temperature for overnight, yielding estradiol diacetate stoichiometrically. Estradiol diacetate was heated at 80° C. in nitrobenzene for 1 hour in the presence of 2 mol equivalent of aluminum chloride and 0.4 mol equivalent of acetyl chloride, and then 2-acetylestradiol 17-acetate was obtained by 85% yield. 2-Acetylestradiol 17-acetate was reacted with hydrogen peroxide at room temperature for 2 hours maintaining pH in a range between 12.0 and 12.5 by the addition of sodium hydroxide and 2-hydroxyestradiol 17-acetate thus obtained was hydrolyzed by conventional method either in acidic or alkaline condition to form 2-hydroxyestradiol by overall yield of 77%.

Workup

  1. customthus obtained

Sources & evidence

ORD record
ord-8b22587100b84131a0b136a0bdd4565e
Source dataset
uspto-grants-1998_04
Patent number
US05739302

Reaction notes

Loading…