Dimethyl Sulfate → Methyl 5-chloro-2-methoxybenzoate

HRID 330289Notes

Reaction equation

HRID 330289 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5](O)=[CH:4][CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].S([O:23][CH3:24])(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:12])=[O:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 94475-Chlorosalicylic AcidHCID 11430Potassium Carbonate

Product 1

HCID 118574Methyl 5-chloro-2-methoxybenzoateYield 99.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-chlorosalicylic acid (20.0 g, 0.116 mol), potassium carbonate (40.3 g, 0.290 mol), and dimethyl sulfate (36.5 g, 0.290 mol) in acetone (300 mL) was heated at reflux for 18 hours. The mixture was cooled, concentrated, diluted with H2O, and extracted with ethyl acetate (3×150 mL). The extracts were washed with H2O and saturated NaCl, dried (MgSO4), and concentrated to give 23.10 g (99%) of product as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. additiondiluted with H2O
  6. extractionextracted with ethyl acetate (3×150 mL)
  7. washThe extracts were washed with H2O and saturated NaCl
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4b72682b21734a0ab04087188b707e53
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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