Dimethyl Sulfate → 2,6-Dimethylanisole

HRID 1488448Notes

Reaction equation

HRID 1488448 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[OH:11].S(OC)(O[CH3:16])(=O)=O>O>[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[O:11][CH3:16]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 113352,6-DimethylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 660882,6-DimethylanisoleYield 57.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide (20 g, 500 mmol) was dissolved in distilled water (200 mL) and placed in a round-bottom flask fitted with a reflux condenser. To the solution were added sequentially 2,6-dimethylphenol (1, 61 g, 500 mmol) and dimethyl sulfate (48 mL, 500 mmol). The mixture was heated at 60° C. for about 17 h, cooled, and transferred to a separatory funnel. The organic layer was separated, and the aqueous layer was extracted with benzene. The combined organic layers were washed sequentially with 10% aq. sodium hydroxide and brine, and dried (MgSO4). Concentration of the solution gave 2,6-dimethylanisole (2, 39 g, 57% yield), bp 179°-182° C./750 torr (lit.: Burton, G. W.; Joyce, A.; Ingold, K. U. Arch. Biochem. Biophys., 1982, 221, 281; 181° C.), as a colorless oil.

Workup

  1. customplaced in a round-bottom flask
  2. customfitted with a reflux condenser
  3. temperaturecooled
  4. customtransferred to a separatory funnel
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with benzene
  7. washThe combined organic layers were washed sequentially with 10% aq. sodium hydroxide and brine
  8. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-2cb75ab397aa4737bdba7e318eb5fd8e
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Reaction notes

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