Dimethyl Sulfate → HCID 13202693, compound

HRID 1197533Notes

Reaction equation

HRID 1197533 reaction equation
[CH2:1]1[C@@H:14]2[C@@:5]([C:15]([OH:17])=[O:16])([C:6]3[C:11]([CH2:12][CH2:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH:3]=[CH:2]1.[CH3:18]OS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]1[CH:14]2[C:5]([C:15]([O:17][CH3:18])=[O:16])([C:6]3[C:11]([CH2:12][CH2:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 11430Potassium Carbonate2×HCID 15657729HCID 15657729, compound

Product 1

HCID 13202693HCID 13202693, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of cis-1,9,10,10a-tetrahydro-4a(4H)-phenanthrenecarboxylic acid (25 g, 0.11 mole) and dimethylsulfate (11.4 ml, 0.12 mole) in 75 ml acetone was treated with potassium carbonate (20.7 g, 0.15 mole) and stirred overnight. An additional 5 ml dimethylsulfate was added and the reaction mixture was refluxed for 1 hour. After cooling the potassium carbonate was removed by filtration and the filtrate evaporated to give the title compound (27 g, quantitative).

Workup

  1. temperaturethe reaction mixture was refluxed for 1 hour
  2. customwas removed by filtration
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-cb8ce54e5ec34a5bafdd0885794c2138
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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