Hydrochloric Acid → Methyl 5-acetyl-2-methoxybenzoate

HRID 1441142Notes

Reaction equation

HRID 1441142 reaction equation
[C:1]([C:4]1[CH:12]=[C:8](C(O)=O)[C:7](O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:14](=[O:17])([O-])[O-:15].[K+].[K+].I[CH3:21].Cl.CN([CH:26]=[O:27])C>>[CH3:21][O:15][C:14](=[O:17])[C:8]1[CH:12]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=[CH:6][C:7]=1[O:27][CH3:26]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 831515-Acetylsalicylic acid

Product 1

HCID 606426Methyl 5-acetyl-2-methoxybenzoate

Procedure

A mixture of 5-acetyl salicylic acid (1.46 g), DMF (10 ml), and potassium carbonate (1.1281 g) is stirred at 20°-25° while adding iodomethane (1.55 ml) via pipette. The reaction mixture is placed under a nitrogen atmosphere and stirred at 20°-25° for 65 hr. Additional iodomethane (0.76 ml) and potassium carbonate (1.14 g) were added, and the reaction is permitted to stir for another 24 hr. The reaction mixture is poured onto 35 ml of 1N hydrochloric acid and extracted with 3.35 ml portions of ether. The organic layers were combined and washed with cold water and cold sodium bicarbonate before being dried with sodium sulfate. Solvent is removed under reduced pressure giveing a solid which is placed in the oven (40°, 0.05 mm) for 24 hours to give the title compound, mp 72°-74°; NMR (CDCl3, TMS) 8.41, 8.12, 7.03, 3.98, 3.92, 2.59δ.

Workup

  1. stirringstirred at 20°-25° for 65 hr
  2. stirringto stir for another 24 hr
  3. extractionextracted with 3.35 ml portions of ether
  4. washwashed with cold water and cold sodium bicarbonate
  5. dry with materialbefore being dried with sodium sulfate
  6. customSolvent is removed under reduced pressure

Sources & evidence

ORD record
ord-27b185402e3e4cdebc71b770aeffcf68
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

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