Dimethyl Sulfate → 1-Chloro-2-methoxy-4-methylbenzene

HRID 734748Notes

Reaction equation

HRID 734748 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[C:10](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 120082-Chloro-5-methylphenol

Product 1

HCID 993521-Chloro-2-methoxy-4-methylbenzeneYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2-Chloro-5-methylphenol (5.00 g, 35.0 mmol, 1.00 equiv) and potassium carbonate (29.0 g, 2.10 mol, 6 equiv) were combined in DMF and stirred 15 minutes. Dimethyl sulfate (9.95 mL, 1.05 mol, 3.00 equiv) was added and the mixture was heated to 70° C. After 1 hour, the reaction was cooled to room temperature and stirred an additional 18 hours. The mixture was diluted with 200 mL H2O and extracted with Et2O. The organic phase was washed three times with H2O and once with brine, then dried over MgSO4 and concentrated en vacuo. 5.48 g (100%) of the product was obtained as a red liquid. 1H NMR (400 MHz, CDCl3) 7.25 (d, 1H), 6.77 (s, 1H), 6.73 (d, 1H), 3.91 (s, 3H), 2.56 (s, 3H).

Workup

  1. waitAfter 1 hour
  2. temperaturethe reaction was cooled to room temperature
  3. stirringstirred an additional 18 hours
  4. extractionextracted with Et2O
  5. washThe organic phase was washed three times with H2O
  6. dry with materialonce with brine, then dried over MgSO4
  7. concentrationconcentrated en vacuo

Sources & evidence

ORD record
ord-7169dea1730345919a65fd853ee89e1e
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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