Hydrochloric Acid → 3-Ethoxy-4-methoxybenzoic acid

HRID 1934724Notes

Reaction equation

HRID 1934724 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:7]([O:9]C)=[O:8])[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:7]([OH:9])=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10536413Methyl 3-ethoxy-4-methoxybenzoate

Product 1

HCID 28229573-Ethoxy-4-methoxybenzoic acidYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-ethoxy-4-methoxybenzoate (4.42 g), methanol (160 mL) and IN-sodium hydroxide solution (40 mL) was heated for 2 hours under reflux. The reaction mixture was acidified with 1N-hydrochloric acid to pH 4, and the organic solvent was removed by evaporation. The aqueous layer was diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with hexane to give 3-ethoxy-4-methoxybenzoic acid as colorless powders (3.76 g). NMR (CDCl3, δ): 1.50 (3H, t, J=7 Hz), 3.95 (3H, s), 4.17 (2H, q, J=7 Hz), 6.92 (1H, d, J=8 Hz), 7.60 (1H, d, J=4 Hz), 7.76 (1H, dd, J=4, 8 Hz); Mass m/z: 195(M+).

Workup

  1. temperatureunder reflux
  2. customthe organic solvent was removed by evaporation
  3. additionThe aqueous layer was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-89705aedfb904e96b30ec0b8851a354c
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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