Methanol → Estrone

HRID 1578752Notes

Reaction equation

HRID 1578752 reaction equation
CO.[OH-].[K+].[CH3:5][C@@:6]12[C:22](=[O:23])[CH2:21][CH2:20][C@H:19]1[C@H:18]1[C@@H:9]([C:10]3[CH:11]=[CH:12][C:13]([OH:24])=[CH:14][C:15]=3[CH2:16][CH2:17]1)[CH2:8][CH2:7]2.S(OC)(O[CH3:29])(=O)=O>O>[CH3:29][O:24][CH3:13].[CH3:5][C@@:6]12[C:22](=[O:23])[CH2:21][CH2:20][C@H:19]1[C@H:18]1[C@@H:9]([C:10]3[CH:11]=[CH:12][C:13]([OH:24])=[CH:14][C:15]=3[CH2:16][CH2:17]1)[CH2:8][CH2:7]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 16 ml of 30% aqueous solution of potassium hydroxide, 1.0 g of estrone was dissolved and the mixture was cooled in an ice bath and stirred while 4 ml of dimethyl sulfate was added. Stirring was continued for 2 hours. Water was added to the reaction mixture and the crystals which precipitated during the addition of water were filtered, washed with water and dried to obtain 0.341 g of the 96.3% purity methyl ether of estrone in a 34.2% yield.

Workup

  1. dissolutionwas dissolved
  2. temperaturethe mixture was cooled in an ice bath
  3. additionwas added
  4. customthe crystals which precipitated during the addition of water
  5. filtrationwere filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-30d7feee3b064c5daac48a9e6a09661d
Source dataset
uspto-grants-1976_02
Patent number
US03939186

Reaction notes

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