Methyl Salicylate → Methyl 2-(2-methoxy-2-oxoethoxy)benzoate

HRID 1957812Notes

Reaction equation

HRID 1957812 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C([O-])([O-])=O.[K+].[K+].Cl[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CC(C)=O>[CH3:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH2:19][C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 7295Methyl chloroacetateHCID 11430Potassium Carbonate

Product 1

HCID 11287524Methyl 2-(2-methoxy-2-oxoethoxy)benzoateYield 17%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of methyl salicylate (100 g, 657 mmol) and anhydrous K2CO3 (360 g, 2.605 mol) in anhydrous acetone (1000 ml) was added methyl chloroacetate (94 g, 866 mmol) and refluxed for 36 hours. The acetone was distilled off and water (1200 ml) was added. Crude 1 was extracted into chloroform, dried over Na2SO4 distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 1 (25 grams, 17%) as a light yellow syrup.

Workup

  1. temperaturerefluxed for 36 hours
  2. distillationThe acetone was distilled off
  3. additionwater (1200 ml) was added
  4. extractionCrude 1 was extracted into chloroform
  5. dry with materialdried over Na2SO4
  6. distillationdistilled
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d78047c6a2dc4171a52c7dbb51d75865
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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