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

HRID 2104248Notes

Reaction equation

HRID 2104248 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[CH3:10]OS(OC)(=O)=O.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 120082-Chloro-5-methylphenol

Product 1

HCID 993521-Chloro-2-methoxy-4-methylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-chloro-5-methylphenol (14.2 g, 1 equiv), Me2SO4 (10.5 mL, 1.1 equiv) and K2CO3 (27.6 g, 2 equiv) in 150 mL of THF was stirred at rt overnight. Ethyl acetate and water were added and the organic layer was dried over sodium sulfate, filtered and evaporated to give 2-chloro-5-methylanisole as a crude product.

Workup

  1. dry with materialthe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-f7ccf0fff05945de8c1d9fa1459c3b0b
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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