Hydrochloric Acid → Benzoic acid, 3-methoxy-4-methyl-, methyl ester

HRID 1198186Notes

Reaction equation

HRID 1198186 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([OH:8])=[O:7].Cl.[CH3:14]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([O:8][CH3:14])=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 815794-Methyl-m-anisic acid

Product 1

HCID 591123Benzoic acid, 3-methoxy-4-methyl-, methyl ester

Procedure

A solution of 3-methoxy-4-methylbenzoic acid (10 grams) in 200 mL of methanol was saturated with hydrochloric acid gas. The resulting solution was warmed on a steam bath for 4 hours. The reaction was allowed to cool and the methanol was evaporated. The residue was dissolved in ethyl acetate and the ethyl acetate layer was washed with water, dried over sodium sulfate and evaporated to give the title compound. NMR (CDCl3) δ:2.15 (s, 3H), 3.80 (s, 3H), 7.48-7.18 (m, 3H).

Workup

  1. temperatureThe resulting solution was warmed on a steam bath for 4 hours
  2. temperatureto cool
  3. customthe methanol was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe ethyl acetate layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-2bd29b1c23174690bb2f554fcd912cc4
Source dataset
uspto-grants-1994_01
Patent number
US05280039

Reaction notes

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