Dimethyl Sulfate → HCID 20513512, compound

HRID 1164040Notes

Reaction equation

HRID 1164040 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11].S(OC)(O[CH3:21])(=O)=O>[OH-].[K+]>[CH3:21][O:11][C:10]1[C:9]([CH3:12])=[CH:8][CH:7]=[CH:6][C:5]=1[O:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 20513456HCID 20513456, compound

Product 1

HCID 20513512HCID 20513512, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Aqueous solution (50 ml) of potassium hydroxide (10.4 g) was added portionwise to a mixture of 6-(2-fluorophenoxy)-o-cresol (13.5 g) and dimethyl sulfate (15.5 g) with stirring under ice-cooling, and the mixture was refluxed under heating for an hour. After cooling, the reaction mixture was extracted with n-hexane, and the extract was washed with 10% aqueous sodium hydroxide and water, dried and then evaporated. The residue was purified by column chromatography (silica gel, benzene.n-hexane) to give oily 2-fluorophenyl 2-methoxy-3-methylphenyl ether (11.6 g).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for an hour
  4. temperatureAfter cooling
  5. extractionthe reaction mixture was extracted with n-hexane
  6. washthe extract was washed with 10% aqueous sodium hydroxide and water
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography (silica gel, benzene.n-hexane)

Sources & evidence

ORD record
ord-1aa4ed7fe2b44926ac7ae2d7dfd79172
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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