Sodium hydride → Methyl 2-(2-methoxycarbonyl-6-acetylphenoxy)propionate

HRID 1761932Notes

Reaction equation

HRID 1761932 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[OH:14])(=[O:3])[CH3:2].[H-].[Na+].Br[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20]>CN(C)C=O>[CH3:10][O:9][C:7]([C:6]1[CH:11]=[CH:12][CH:13]=[C:4]([C:1](=[O:3])[CH3:2])[C:5]=1[O:14][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionateHCID 13037297Methyl 3-acetyl-2-hydroxybenzoate

Product 1

HCID 20043643Methyl 2-(2-methoxycarbonyl-6-acetylphenoxy)propionateYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.3 g of methyl 3-acetylsalicylate are dissolved in 50 ml of dimethylformamide and the solution is added dropwise to a suspension of 1.26 g of 62.5% sodium hydride in 15 ml of dimethylformamide, and the mixture is stirred for 20 minutes. 5.40 g of methyl 2-bromo-propionate are added dropwise to the mixture and the mixture is heated at 60°-80° C. for 7 hours. The reaction mixture is poured into ice-water and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=3:1) to give 5.10 g of methyl 2-(2-methoxycarbonyl-6-acetylphenoxy)propionate as colorless oil.

Workup

  1. temperaturethe mixture is heated at 60°-80° C. for 7 hours
  2. extractionthe aqueous mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-cbcff5c86bd34831a845ae99533f06bb
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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