Hydrochloric Acid → Methyl 5-acetyl-2-methoxybenzoate

HRID 421069Notes

Reaction equation

HRID 421069 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:5](=[CH:7][CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)[OH:6].[C:15](=O)([O-])[O-].[Na+].[Na+].CI.Cl>O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[CH:8]=[CH:7][C:5]=1[O:6][CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 606426Methyl 5-acetyl-2-methoxybenzoateYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-acetylsalicylic acid methyl ester (5.00 g, 25.7 mmol), sodium carbonate (7.10 g, 51.4 mmol) and N,N-dimethylformamide (25 mL) was cooled with ice bath. Methyl iodide (2.5 mL, 40.1 mmol) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water, neutralized by hydrochloric acid, and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was washed under suspension (isopropyl ether/n-hexane) to give the title compound (5.17 g, 96.5%) as a white crystal.

Workup

  1. temperaturewas cooled with ice bath
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation under reduced pressure
  6. washwas washed under suspension (isopropyl ether/n-hexane)

Sources & evidence

ORD record
ord-d4c6d122a4724c71834aac6b7ed16e3f
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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