Methyl iodide → 3-Benzyloxy-6-methoxypicolinic acid

HRID 49431Notes

Reaction equation

HRID 49431 reaction equation
CI.CCCCCC.CC(C)=O.[CH2:13]([O:20][C:21]1[C:22]([C:29]([O:31]C)=[O:30])=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O[Li].O>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:13]([O:20][C:21]1[C:22]([C:29]([OH:31])=[O:30])=[N:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 168937Lithium hydroxide, monohydrateHCID 21880519Acetone hexaneHCID 22175139Methyl 3-benzyloxy-6-methoxypicolinate

Product 1

HCID 178176343-Benzyloxy-6-methoxypicolinic acid

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of this compound (10.25 g) in toluene (125 mL), warmed in an oil bath at 60° C., was added silver carbonate (16.6 g), then methyl iodide (8.52 g). The resulting mixture was stirred and heated for 3 hours at 60° C. After cooling, the mixture was filtered through Celite® and the solvent evaporated to give a yellow oil. Silica gel chromatography (4:1 hexane/acetone) gave a nearly colorless oil, whose 1H-NMR and MS data were consistent with methyl 3-benzyloxy-6-methoxypicolinate. Hydrolysis of this ester to the title acid 18 was accomplished with LiOH.H2O as described above for related esters.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through Celite®
  3. customthe solvent evaporated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-f82f0be578eb468b9834a285f41dd5f3
Source dataset
uspto-grants-2004_03
Patent number
US06706740B2

Reaction notes

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