Methanol → Methyl 4-(4-pyridinyl)benzoate

HRID 1264209Notes

Reaction equation

HRID 1264209 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.OS(O)(=O)=O.[OH-].[Na+].[CH3:23]O>>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([O:13][CH3:23])=[O:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 15208114-(Pyridin-4-yl)benzoic acid

Product 1

HCID 5152686Methyl 4-(4-pyridinyl)benzoate

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[pyridin-4-yl]-benzoic acid (2.0 g, 10 mmol) (reference example 11a) in methanol (30 mL) is added conc. H2SO4 (4 mL). The resulting solution is warmed to 60° C. and stirred at this temperature for 2.5 hours. The reaction mixture is then allowed to cool to room temperature then poured into ice. The pH of the resulting solution is adjusted to 7 using a 10 M solution of NaOH. The product is then extracted into ethyl acetate. This solution is washed with brine, dried over MgSO4 and concentrated to give 2.1 g of the title compound as a white solid. 1H NMR (CDCl3) d 3.94 (s, 3H), 7.50 (d, J=5 Hz, 2H), 7.69 (d, J=8 Hz, 2H), 8.13 (d, J=5 Hz, 2H) 8.68 (d, J=5 Hz, 2H). MS (EI) m/z 213 (M)+.

Workup

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

Sources & evidence

ORD record
ord-d040d0eaa30443eb922b24e3d6650d50
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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