Dimethyl Sulfate → Methyl 2-methoxy-3-methylbenzoate

HRID 2186636Notes

Reaction equation

HRID 2186636 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[OH:11].[C:12](=O)([O-])[O-].[K+].[K+].COS([O:23][CH3:24])(=O)=O>CC(C)=O>[CH3:12][O:11][C:3]1[C:2]([CH3:1])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:23][CH3:24])=[O:7]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 67383-Methylsalicylic AcidHCID 11430Potassium Carbonate

Product 1

HCID 13229229Methyl 2-methoxy-3-methylbenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3-methyl-salicylic acid (1.32 mol)and anhydrous potassium carbonate (3.6 mol)dissolved in 3.5 L of dry acetone in a 5L round bottle flask, dimethylsulfate (2.2 mol) was added in several times. The mixture was refluxed overnight, and the reaction was monitored by TLC. After filtration of the reaction mixture, the solvents of the filtrate were evaporated and 215 g of a pale yellow thick oil was obtained as the raw product. Yield 91%. 1H NMR (500 MHz, CDCl3, 25° C.) δ: 2.263 (s, 3H, CH3), 3.782 (s, 3H, OCH3), 3.854 (s, 3H, OCH3), 6.984 (t, J=7.5, 1H, ArH), 7.276 (d, J=7.5, 1H, ArH), 7.582 (d, J=7.5, 1H, ArH); 13C NMR (500 MHz, CDCl3, 25° C.) δ: 15.72, 51.81, 61.17, 123.26, 124.36, 128.86, 132.46, 134.88, 158.16, 166.61.

Workup

  1. additionwas added in several times
  2. temperatureThe mixture was refluxed overnight
  3. filtrationAfter filtration of the reaction mixture
  4. customthe solvents of the filtrate were evaporated

Sources & evidence

ORD record
ord-fcf342dbae20466ea760de9c24770926
Source dataset
uspto-grants-2002_06
Patent number
US06406297B1

Reaction notes

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