Estrone → Estrone

HRID 1578756Notes

Reaction equation

HRID 1578756 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.S(OC)(OC)(=O)=O.[O:28]1[CH2:33]COC[CH2:29]1.[OH-].[Na+]>O>[CH3:29][O:28][CH3:33].[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2

Participants

7

Reactant 4

HCID 5870EstroneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 312751,4-Dioxane

Product 2

HCID 5870EstroneHCID 8254Dimethyl Ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a mixture of 1 g of estrone, 0.5 ml of dimethyl sulfate and 5 ml of dioxane, 5 ml of 10% NaOH aqueous solution was added over a period of one hour. The reaction temperature was maintained at 15° - 20°C. The resulting mixture was stirred for one hour. Then, 30 ml of water was added and the resulting cyrstals were filtered, washed with water and dried to obtain 1.040 g of the 100% purity methyl ether of estrone in a 98.9% yield.

Workup

  1. additionwas added over a period of one hour
  2. temperatureThe reaction temperature was maintained at 15° - 20°C
  3. filtrationthe resulting cyrstals were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-23de78ef4dd245338ba5d6805e31ede6
Source dataset
uspto-grants-1976_02
Patent number
US03939186

Reaction notes

Loading…