Methanol → Methyl 4-(4-pyridinyl)benzoate

HRID 459542Notes

Reaction equation

HRID 459542 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:22]O>>[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([O:14][CH3:22])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 574326074-(Pyridin-4-yl)benzoic acid hydrochloride

Product 1

HCID 5152686Methyl 4-(4-pyridinyl)benzoate

Procedure

4-(4-Pyridyl)benzoic acid hydrochloride (12.4 g) was dissolved in methanol (200 ml), concentrated sulfuric acid (5 ml) was added at room temperature, and the mixture was heated under reflux for 3 hours. After completion of the reaction, the solvent was distilled off, and a saturated aqueous solution of sodium hydrogencarbonate was added to the residue to extract it with ethyl acetate. The extract was dried over anhydrous sodium sulfate, the solvent was distilled off, and hexane was added to the residue to solidify it, thereby obtaining the title compound (9.86 g) as colorless powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the residue
  6. extractionto extract it with ethyl acetate
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off
  9. additionhexane was added to the residue

Sources & evidence

ORD record
ord-15ba4d104a684ef8a442f3d86b2d30f3
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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