Dimethyl Sulfate → HCID 12557667, compound

HRID 2052381Notes

Reaction equation

HRID 2052381 reaction equation
[OH:1][C:2]1[C:3](=[O:11])[CH:4]=[CH:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C:12](=O)([O-])[O-].[K+].[K+].S(OC)(O[CH3:22])(=O)=O>CC(=O)CC>[CH3:12][O:1][C:2]1[C:3](=[O:11])[CH:4]=[CH:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:22][O:11][C:3]1[C:2](=[O:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178491502HCID 178491502, compound

Product 2

HCID 12557667HCID 12557667, compoundHCID 12557668HCID 12557668, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-hydroxy-4-methoxy-2,4,6-cycloheptatrien-1-one (described above, 13 g), potassium carbonate (23.6 g), dimethyl sulfate (21.6 g) and 2-butanone (130 ml) is heated at reflux for 3 hours. The mixture is filtered and the filtrate is evaporated. The residue is subjected to chromatography on silica gel using acetone-ethyl acetate (1:1) and evaporation of the eluates gives 2,4-dimethoxy-2,4,6-cycloheptatrien-1-one and 2,6-dimethoxy-2,4,6-cycloheptatrien-1-one.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. customacetone-ethyl acetate (1:1) and evaporation of the eluates

Sources & evidence

ORD record
ord-d572b706f9a24e909a1131102f6aec27
Source dataset
uspto-grants-1980_01
Patent number
US04183955

Reaction notes

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