Methanol → Methyl 4-(4-pyridinyl)benzoate

HRID 1675093Notes

Reaction equation

HRID 1675093 reaction equation
S(Cl)(Cl)=O.[N:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([O-:17])=[O:16])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[Na+].[CH3:21]O>>[N:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([O:17][CH3:21])=[O:16])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 23673507Sodium 4-(pyridin-4-yl)benzoate

Product 1

HCID 5152686Methyl 4-(4-pyridinyl)benzoateYield 86%

Conditions

Temperature
65 °C

Procedure

Thionyl chloride (683 mL, 9358.59 mmol) was added dropwise over 20 minutes to a suspension of sodium 4-(pyridin-4-yl)benzoate (690 g, 3119.53 mmol) in methanol (15 L) at −10° C., keeping the temperature below 15° C. The mixture was stirred for 10 minutes then heated to 65° C. for 15 hours. The reaction mixture was cooled to 20° C. and the solvent was evaporated. The solid residue was partioned between ethyl acetate (14 L) and aqueous saturated sodium bicarbonate solution (14 L). The organic layer was separated and the aqueous layer extracted with ethyl acetate (7 L). The combined organics were washed with water (14 L), saturated brine (7 L) dried over magnesium sulfate, filtered and evaporated to dryness to afford methyl 4-(pyridin-4-yl)benzoate (570 g, 86%) as a solid.

Workup

  1. customthe temperature below 15° C
  2. temperatureThe reaction mixture was cooled to 20° C.
  3. customthe solvent was evaporated
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with ethyl acetate (7 L)
  6. washThe combined organics were washed with water (14 L), saturated brine (7 L)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-5388369abd514fab9683b15fed042e15
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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