Methanol → Estrone

HRID 1578753Notes

Reaction equation

HRID 1578753 reaction equation
CO.S([O:8][CH3:9])(OC)(=O)=O.[CH3:10][C@@:11]12[C:27](=[O:28])[CH2:26][CH2:25][C@H:24]1[C@H:23]1[C@@H:14]([C:15]3[CH:16]=[CH:17][C:18]([OH:29])=[CH:19][C:20]=3[CH2:21][CH2:22]1)[CH2:13][CH2:12]2.[OH-].[K+]>O>[CH3:10][O:8][CH3:9].[CH3:10][C@@:11]12[C:27](=[O:28])[CH2:26][CH2:25][C@H:24]1[C@H:23]1[C@@H:14]([C:15]3[CH:16]=[CH:17][C:18]([OH:29])=[CH:19][C:20]=3[CH2:21][CH2:22]1)[CH2:13][CH2:12]2

Participants

7

Reactant 4

HCID 887MethanolHCID 5870EstroneHCID 6497Dimethyl SulfateHCID 14797Potassium Hydroxide

Product 2

HCID 5870EstroneHCID 8254Dimethyl Ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a mixture of 20 ml of methanol and 4 ml of dimethyl sulfate, 1.0 g of estrone was suspended and the mixture was cooled in an ice bath and stirred while 16 ml of 30% aqueous solution of potassium hydroxide was added over a period of 1 hour. Stirring was continued for 2 hours. Water was added to the reaction mixture, and the precipitated crystals were filtered, washed with water and dried to obtain 1.017 g of the 96.0% purity methyl ether of estrone in a 96.7% yield.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. additionwas added over a period of 1 hour
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-1ee091a1dd304c5eb8a90b1d8c0a79b2
Source dataset
uspto-grants-1976_02
Patent number
US03939186

Reaction notes

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