Methanol → Methyl 3-(3-pyridinyl)benzoate

HRID 2295764Notes

Reaction equation

HRID 2295764 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12](C(=O)CC)[CH2:11]2)[CH:5]=1.[OH-].[Na+].CO>O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12937986HCID 12937986, compound

Product 1

HCID 4133188Methyl 3-(3-pyridinyl)benzoateYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl-3-(1-propionylpiperidin-3-yl)benzoate (4.8 g, 0.017 mol), sodium hydroxide pellets (5 g), methanol (80 ml) and water (20 ml) was stirred until TLC indicated that no starting material remained (4 hours). The methanol was evaporated and the alkaline water layer was washed with ether, acidified with hydrochloric acid and extracted with chloroform. Evaporation gave the product (4.0 g, 69% yield from methyl-3-(3-pyridyl)-benzoate) as an oil which crystallized after several weeks on standing. (Mp. 125°-126° C.).

Workup

  1. custom(4 hours)
  2. customThe methanol was evaporated
  3. washthe alkaline water layer was washed with ether
  4. extractionextracted with chloroform
  5. customEvaporation

Sources & evidence

ORD record
ord-0a3c8f1d8b2a47339c5ddf1b57caf12f
Source dataset
uspto-grants-1984_01
Patent number
US04426386

Reaction notes

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