Hydrochloric Acid → 2-Methoxy-5-(2-oxo-propoxy)-benzoic acid

HRID 2230729Notes

Reaction equation

HRID 2230729 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12](=[O:14])[CH3:13])[CH:7]=[CH:6][C:5]=1[O:15][CH3:16].[OH-].[Na+].Cl>CO>[CH3:16][O:15][C:5]1[CH:6]=[CH:7][C:8]([O:10][CH2:11][C:12](=[O:14])[CH3:13])=[CH:9][C:4]=1[C:3]([OH:17])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 701488462-Methoxy-5-(2-oxo-propoxy)-benzoic acid methyl ester

Product 1

HCID 184645202-Methoxy-5-(2-oxo-propoxy)-benzoic acidYield 80.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir a mixture of 2-methoxy-5-(2-oxo-propoxy)-benzoic acid methyl ester (0.49 g, 2.1 mmol), methanol (20 mL) and 1N NaOH (20 mL, 20 mmol) for two hours at room temperatue. Acidify the reaction with 1N HCl (to pH 2) and extract with dichloromethane. Dry (MgSO4) the organic phase, filter and concentrate the filtrate in vacuo. Purify the residue by column chromatography (silica gel, step gradient elution with 3% methanol in dichloromethane to 10% methanol in dichloromethane and concentrate the appropriate fractions to afford 0.38 g of 2-methoxy-5-(2-oxo-propoxy)-benzoic acid, Rf=0.82 (silica gel, dichloromethane:methanol:acetic acid, 85:10:5).

Workup

  1. extractionextract with dichloromethane
  2. dry with materialDry (MgSO4) the organic phase
  3. filtrationfilter
  4. concentrationconcentrate the filtrate in vacuo
  5. customPurify the residue by column chromatography (
  6. washsilica gel, step gradient elution with 3% methanol in dichloromethane to 10% methanol in dichloromethane
  7. concentrationconcentrate the appropriate fractions

Sources & evidence

ORD record
ord-ef5fbd66c3ae45faa6a768cbe722d5c8
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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