Hydrochloric Acid → 3-Methoxy-4-(pyridin-2-yl)benzoic acid

HRID 7765Notes

Reaction equation

HRID 7765 reaction equation
CO.O.[OH-].[Li+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:11]([O:13]C)=[O:12].Cl>O>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 21990944Methyl 3-methoxy-4-pyridin-2-ylbenzoate

Product 1

HCID 219565153-Methoxy-4-(pyridin-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 154 mL of a 50/50 solution of MeOH and H2O was added lithium hydroxide monohydrate (13.85 g, 330 mmol). The solution was stirred until all of the salt dissolved, at which point methyl 3-methoxy-4-pyridin-2-ylbenzoate (8.02 g, 32.9 mmol) was added. The mixture was heated at reflux and stirred overnight. The reaction mixture was cooled to rt, neutralized with 6N HCl, and acidified to pH 4 with 1N HCl. A colorless solid crashed out of solution and was filtered to give 3-methoxy-4-pyridin-2-ylbenzoic acid as a colorless solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.70 (d, 1H), 7.92–7.84 (m, 3H), 7.69–7.65 (m, 2H), 7.40–7.36 (m, 1H), 3.91 (s, 3H).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureat reflux
  4. stirringstirred overnight
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-78f9376cc45a4226aebdcbd7db6399c9
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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