Methyl chloroacetate → HCID 53919154, compound

HRID 964454Notes

Reaction equation

HRID 964454 reaction equation
[C:1]([C:4]1[CH:13]=[C:8]([C:9]([O:11]C)=[O:10])[C:7]([OH:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl[CH2:16][C:17]([O:19]C)=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:16][C:17]([OH:19])=[O:18])=[C:8]([CH:13]=1)[C:9]([OH:11])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 53919154HCID 53919154, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.16 g of 5-acetylsalicylic acid, methyl ester in 10 mL of N,N-dimethylformamide is added 1 g of chloroacetic acid, methyl ester and 1.2 g of potassium carbonate. After stirring this mixture at ambient temperature for 16 hours the reaction is filtered, diluted with ethyl acetate, and washed once with water and twice with brine. The ethyl acetate is dried with magnesium sulfate, filtered, and evaporated to give 5-acetyl-2-(carboxymethoxy)benzoic acid as a crude product. Crystallization from methanol at -15° C. gives 0.6 g of white crystals. 1H-NMR (CDCl3): 8.5 ppm (1H, d), 8.1 ppm (1H, dd), 6.9 ppm (1H, d), 4.8 ppm (2H, s), 4.0 ppm (3H, s), 3.8 ppm (3H, s), 2.6 ppm (3H, s).

Workup

  1. filtrationis filtered
  2. additiondiluted with ethyl acetate
  3. washwashed once with water and twice with brine
  4. dry with materialThe ethyl acetate is dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-73829f305b6d4ef0a80ef1ed1fb7f681
Source dataset
uspto-grants-1998_06
Patent number
US05767285

Reaction notes

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