Methanol → Methyl 3-(3-pyridinyl)benzoate

HRID 2108197Notes

Reaction equation

HRID 2108197 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, 0.17 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 hydrochloride 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-6ac6228cbc2d421bb4286ecc0219bb68
Source dataset
uspto-grants-1990_06
Patent number
US04937346

Reaction notes

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