Methanol → Methyl 4-pyridin-3-ylbenzoate

HRID 1359600Notes

Reaction equation

HRID 1359600 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH:2]=1.OS(O)(=O)=O.[OH-].[Na+].[CH3:23]O>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([O:13][CH3:23])=[O:12])=[CH:9][CH:8]=2)[CH:2]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15152444-Pyridin-3-yl-benzoic acid

Product 1

HCID 4133187Methyl 4-pyridin-3-ylbenzoate

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[pyridin-3-yl]-benzoic acid (2.2 g, 11 mmol) (reference example 17b) in methanol (33 mL) was added conc. H2SO4 (5 mL). The resulting solution was warmed to 60° C. and stirred at this temperature for 45 min. The reaction mixture was then allowed to cool to room temperature then poured into ice. The pH of the resulting solution was adjusted to 7 using a 10 M solution of NaOH. The product was then extracted into ethyl acetate. This solution was washed with brine, dried over MgSO4 and concentrated to give 1.74 g of the title compound as a tan solid. 1H NMR (CDCl3) d 3.96 (s, 3H), 7.40 (dd, J=8, 5 Hz, 1H), 7.66 (m, 2H), 7.93 (m, 1H), 8.15 (m, 2H), 8.65 (bs, 1H), 8.89 (bs, 1H). MS (EI) m/z 213 (M)+.

Workup

  1. temperatureto cool to room temperature
  2. additionthen poured into ice
  3. extractionThe product was then extracted into ethyl acetate
  4. washThis solution was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ed776be3e264af7af41a2bc58b0bdc3
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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