Hydroxide → Estrone

HRID 1578754Notes

Reaction equation

HRID 1578754 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-]>CO.O1CCCC1.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

8

Reactant 3

HCID 961HydroxideHCID 5870EstroneHCID 6497Dimethyl Sulfate

Product 2

HCID 5870EstroneHCID 8254Dimethyl Ether

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a mixture of 1 g of estrone, 0.5 ml of dimethyl sulfate and 5 ml of tetrahydrofuran, 6 ml of 10% methanolpotassium hydroxide solution was added over a period of 1 hour. The reaction temperature was maintained at 10° - 15°C. The resulting mixture was stirred for one hour to complete the etherification. Then, 15 ml of water was added to the reaction mixture, tetrahydrofuran and methanol were distilled off under atmospheric pressure. The residue was extracted with chloroform, washed with water, and dried. Evaporation of chloroform yielded 1.032 g of the 100% purity methyl ether of estrone in a 98.4% yield.

Workup

  1. additionwas added over a period of 1 hour
  2. temperatureThe reaction temperature was maintained at 10° - 15°C
  3. distillationwere distilled off under atmospheric pressure
  4. extractionThe residue was extracted with chloroform
  5. washwashed with water
  6. customdried
  7. customEvaporation of chloroform

Sources & evidence

ORD record
ord-9a019c57b832489c8cae04cf983fe665
Source dataset
uspto-grants-1976_02
Patent number
US03939186

Reaction notes

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