Benzyl Alcohol → 6-((Benzyloxy)carbonyl)picolinic acid

HRID 1397288Notes

Reaction equation

HRID 1397288 reaction equation
[N:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1[C:10]([OH:12])=[O:11].[CH2:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.OS(O)(=O)=O>O>[CH2:13]([O:11][C:10]([C:2]1[N:1]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=[CH:4][CH:3]=1)=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 103672,6-Pyridinedicarboxylic acid

Product 1

HCID 153299296-((Benzyloxy)carbonyl)picolinic acidYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,6-pyridinedicarboxylic acid (10 g, 0.06 mol) and benzyl alcohol (68 mL, 0.66 mol) were taken in water (25 mL), and concentrated H2SO4 (3.5 mL) was added. The reaction mixture was refluxed for 10 h and further allowed to stir at room temperature for 24 h. The reaction mixture was concentrated under reduced pressure and the organic product was extracted with CHCl3. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% MeOH in CH2Cl2) to afford 6-((benzyloxy)carbonyl)picolinic acid (4.6 g, yield 30%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.54 (br s, 1H), 8.29-8.24 (m, 2H), 8.20-8.16 (m, 1H), 7.52-7.50 (m, 2H), 7.44-7.36 (m, 3H), 5.43 (s, 2H). MS (ESI) m/z: Calculated for C14H11NO4: 257.07. found: 258.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe organic product was extracted with CHCl3
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-781e6510ec674b579a8ba234add069fd
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…