Dimethyl Sulfate → HCID 12557643, compound

HRID 1703823Notes

Reaction equation

HRID 1703823 reaction equation
[OH:1][C:2]1[C:3](=[O:16])[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:17](=O)([O-])[O-].[K+].[K+].[CH3:23]OS(OC)(=O)=O>C(C(C)=O)C>[CH3:17][O:1][C:2]1[C:3](=[O:16])[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:23][O:16][C:3]1[C:2](=[O:1])[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 12557640HCID 12557640, compound

Product 2

HCID 12557643HCID 12557643, compoundHCID 12557644HCID 12557644, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-hydroxy-3-phenoxy-2,4,6-cycloheptatriene-1-one (13.0 g, described by Y. Kitahara, Sci. Repts. Tohoku Univ. First Ser., 39, 265-74 (1956), (CA 51, 12874f)], potassium carbonate (28.9 g), dimethylsulfate (26.5 g) and methyl ethyl ketone (680 ml) is heated at reflux for two hours. The hot mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is subjected to chromatography on silica gel using ether. The appropriate fractions of the eluate are combined and evaporated to give 2-methoxy-3-phenoxy-2,4,6-cycloheptatrien-1-one and 2-methoxy-7-phenoxy-2,4,6-cycloheptatrien-1-one.

Workup

  1. temperatureat reflux for two hours
  2. filtrationThe hot mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure
  4. customevaporated

Sources & evidence

ORD record
ord-96c01f123234483a8a9e1fb4b62e50a3
Source dataset
uspto-grants-1978_11
Patent number
US04125625

Reaction notes

Loading…