Dimethyl Sulfate → 2-Methoxy-4,6-dimethylbenzaldehyde

HRID 1382163Notes

Reaction equation

HRID 1382163 reaction equation
COS([O:6][CH3:7])(=O)=O.C(=O)([O-])[O-].[K+].[K+].[CH3:14][C:15]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19](O)[C:16]=1[CH:17]=[O:18]>CC(C)=O>[CH3:14][C:15]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([O:6][CH3:7])[C:16]=1[CH:17]=[O:18]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 591070HCID 591070, compound

Product 1

HCID 132374732-Methoxy-4,6-dimethylbenzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dimethylsulfate (16.4 g; 130 mmole) and potassium carbonate (20.7 g; 150 mmole) were added to a solution of 2,4-dimethyl-6-hydroxybenzaldehyde (20.0 g; 130 mmole) in acetone (200 ml). The mixture was heated under reflux with stirring for 48 hours and then evaporated to dryness. The residue was dissolved in dichloromethane and washed successively with water, aqueous sodium hydroxide (1M) and water, and then was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 2,4-dimethyl-6-methoxybenzaldehyde (18.9 g; 89.0%). The product was obtained as a brown oil and was characterized by its proton magnetic resonance spectrum, the details of which are recorded in Table 2 below.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed successively with water, aqueous sodium hydroxide (1M) and water
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7cd7d6eee54f4e5097735b918ef06ccc
Source dataset
uspto-grants-1989_02
Patent number
US04806141

Reaction notes

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