Estrone → Estrone

HRID 1578757Notes

Reaction equation

HRID 1578757 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)(O[CH3:25])(=O)=O.[OH-].[Na+]>C(C(C)=O)C.O>[CH3:25][O:20][CH3:9].[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 3

HCID 5870EstroneHCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide

Product 2

HCID 5870EstroneHCID 8254Dimethyl Ether

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

Into a mixture of 1 g of estrone, 0.5 ml of dimethyl sulfate and 10 ml of methyl ethyl ketone, 5 ml of the 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 1 hour. 10 ml of water was added to the reaction mixture and methyl ethyl ketone was distilled off. The crystals which formed during the distillation were filtered from the cooled reaction mixture, washed with water and dried to obtain 1.037 g of the 100% purity methyl ether of estrone in a 98.6% yield.

Workup

  1. additionwas added over a period of one hour
  2. temperatureThe reaction temperature was maintained at 15° - 20°C
  3. distillationwas distilled off
  4. customThe crystals which formed during the distillation
  5. filtrationwere filtered from the cooled reaction mixture
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-400767ea046e479097ebba87051faec8
Source dataset
uspto-grants-1976_02
Patent number
US03939186

Reaction notes

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