Methyl Salicylate → HCID 10979618, compound

HRID 129388Notes

Reaction equation

HRID 129388 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Br[CH2:13][C:14]1[N:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:21][O:20][C:18]1[CH:17]=[C:16]([O:22][CH3:23])[N:15]=[C:14]([CH2:13][O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([O:10][CH3:11])=[O:9])[N:19]=1

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 11430Potassium CarbonateHCID 14493324HCID 14493324, compound

Product 1

HCID 10979618HCID 10979618, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.52 g of methyl salicylate, 2.33 g of 2-bromomethyl-4,6-dimethoxypyrimidine and 1.6 g of potassium carbonate were stirred in 20 ml of dimethylformamide at 60° C. for 2 hours. The reaction mixture was poured in ice water and extracted with ethyl acetate. The extract was dried over sodium sulfate and, after distilling off the solvent, purified using silica gel chromatography to obtain 2.5 g of methyl 2-(4,6-dimethoxy-2-pyrimidyl)methyloxybenzoate (yield 82%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. distillationafter distilling off the solvent
  4. custompurified

Sources & evidence

ORD record
ord-7c6bdcd562ee4b75945f1300a778b4b1
Source dataset
uspto-grants-1995_11
Patent number
US05468721

Reaction notes

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