Dimethyl Sulfate → HCID 20738653, compound

HRID 2401471Notes

Reaction equation

HRID 2401471 reaction equation
[OH:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].[C:15]([O-])([O-])=O.[K+].[K+].COS([O:26][CH3:27])(=O)=O>CC(C)=O>[CH3:15][O:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:26][CH3:27])=[O:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 190169231403597-59-0

Product 1

HCID 20738653HCID 20738653, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the crude 3-hydroxy-2-methyl-4-nitrobenzoic acid in acetone (300 mL) was added K2CO3 (15.8 g, 115 mmol) and Me2SO4 (8.7 g, 69 mmol). The mixture was refluxed at 60° C. for 2 h. After the solvent was evaporated in vacuo, the resulting residue was purified by silica gel-column (eluting with PE/EA=10:1) to afford methyl 3-methoxy-2-methyl-4-nitrobenzoate as a yellowish solid (2.7 g, 33% yield, two steps). m/z (ES+APCI)+: [M+H]+226.1.

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. customthe resulting residue was purified by silica gel-column (eluting with PE/EA=10:1)

Sources & evidence

ORD record
ord-50cc9a8c81f8400e9ac1e37741c82167
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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