Benzyl Alcohol → 2-(Benzyloxy)pyridine-4-carboxylic acid

HRID 333812Notes

Reaction equation

HRID 333812 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[CH2:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O[K])(C)(C)C.O>CN1C(=O)CCC1>[CH2:11]([O:18][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 2369852-Chloroisonicotinic acidHCID 178418922HCID 178418922, compound

Product 1

HCID 229262722-(Benzyloxy)pyridine-4-carboxylic acidYield 71.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

2-Chloro isonicotinic acid (9.45 g) and benzyl alcohol (12.977 g) were dissolved in NMP (180 mL), and treated with tBuOK (20.2 g) between 10-25° C. The reaction mixture was then stirred at 125° C. (Bath-temperature) for 6 h, cooled down to r.t., poured into water (1500 ml) and extracted twice with water. The combined aqueous phases were treated with concentrated aqueous HCl until pH 3 (16 ml). After 10 min the solid was filtered, washed with water and dried under high vacuum, to give the title compound as an off-white solid (9.8 g). MS (m/e)=228.1 (M−H).

Workup

  1. temperaturecooled down to r.t.
  2. extractionextracted twice with water
  3. additionThe combined aqueous phases were treated with concentrated aqueous HCl until pH 3 (16 ml)
  4. filtrationAfter 10 min the solid was filtered
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-82ae8e39b44a4d4682ea5910c4ad8050
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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