Dimethyl Sulfate → 2,3-Dimethoxy-6-nitrobenzaldehyde

HRID 580036Notes

Reaction equation

HRID 580036 reaction equation
[K].[OH:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([N+:13]([O-:15])=[O:14])[C:4]=1[CH:5]=[O:6].[C:16](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.[K]>CC(C)=O>[CH3:16][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([N+:13]([O-:15])=[O:14])[C:4]=1[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 6497Dimethyl Sulfate2×HCID 11430Potassium CarbonateHCID 5462222PotassiumHCID 867411922-Hydroxy-3-methoxy-6-nitrobenzaldehyde potassium salt

Product 1

HCID 71721272,3-Dimethoxy-6-nitrobenzaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Hydroxy-3-methoxy-6-nitrobenzaldehyde potassium salt was slurried in acetone (500 mL) containing potassium carbonate (50 g) and the suspension was treated with dimethylsulfate (18.5 mL) and heated to reflux for one hour. An additional aliquot (18.5 mL) of dimethylsulfate was then added and the mixture was heated overnight. After 24 hours the red color of the potassium salt was virtually absent. The salts were removed by filtration, the filtrate was concentrated and the residue was recrystallized from isopropanol to give the title compound 40.0 g (80% from 3) mp 109°-110° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for one hour
  3. temperaturethe mixture was heated overnight
  4. customThe salts were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-fdb1135aa64f479b9d5ffa1f9f79fafb
Source dataset
uspto-grants-1988_06
Patent number
US04751304

Reaction notes

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