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

HRID 2169690Notes

Reaction equation

HRID 2169690 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-8a6473d787144a71b15abb967c10fd8a
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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