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

HRID 2405166Notes

Reaction equation

HRID 2405166 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:12]([O-])([O-])=[O:13].[K+].[K+].C[C:19]([CH3:21])=[O:20]>>[CH3:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH2:21][C:19]([O:13][CH3:12])=[O:20]

Participants

4

Reactant 3

HCID 180AcetoneHCID 4133Methyl SalicylateHCID 11430Potassium Carbonate

Product 1

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

Procedure

To a mixture of methyl salicylate (100 grams, 657 mmol), anhydrous K2CO3 (360 grams, 2.605 mol) in anhydrous acetone (1000 mL) was added methyl chloro acetate (94 grams, 866 mmol) and refluxed for 36 hours. Acetone was distilled and water (1200 mL) was added. Crude 5 was extracted into Chloroform, dried over Na2SO4 distilled and purified by column chromatography on silica gel using Hexane as eluant to give pure 5 (25 grams, 17%) as a light yellow syrup. The structure was confirmed by NMR. IHNMR (CDCl3) δ 3.79(s, 3H,ester), 3.88(s,3H,ester), 4.70(s,2H,OCH2), 6.88(dd,1H, Ar), 7.03 (m,1H,Ar), 7.42(m,1H,Ar), 7.81(dd,1H,Ar).

Workup

  1. temperaturerefluxed for 36 hours
  2. distillationAcetone was distilled
  3. additionwater (1200 mL) was added
  4. extractionCrude 5 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-ff625e8423ec454b9eee092251ae6664
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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