Dimethyl Sulfate → 3-Methoxy-5-Methylphenol

HRID 2228014Notes

Reaction equation

HRID 2228014 reaction equation
S(OC)(O[CH3:5])(=O)=O.[C:8]1([OH:16])[CH:15]=[C:13]([CH3:14])[CH:12]=[C:10]([OH:11])[CH:9]=1>[OH-].[Na+]>[CH3:5][O:11][C:10]1[CH:9]=[C:8]([OH:16])[CH:15]=[C:13]([CH3:14])[CH:12]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 10436Orcinol

Product 1

HCID 766743-Methoxy-5-MethylphenolYield 43%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Dimethyl sulfate (39 ml; 0.41 mol) was added to a solution of orcinol (64 g; 0.45 mol) in 10% aqueous sodium hydroxide solution (360 ml). The mixture was refluxed for 1½ hours and extracted with ether. The organic phase was evaporated and purified by flash chromatography eluting with dichloromethane/ethanol (98/2) to give 3-methoxy-5-methylphenol. Yield=43%.

Workup

  1. temperatureThe mixture was refluxed for 1½ hours
  2. extractionextracted with ether
  3. customThe organic phase was evaporated
  4. custompurified by flash chromatography
  5. washeluting with dichloromethane/ethanol (98/2)

Sources & evidence

ORD record
ord-1173d9f5f1d848fd8816780a83d37539
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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