Methylparaben → Methyl 4-(pyridin-2-yloxy)benzoate

HRID 230794Notes

Reaction equation

HRID 230794 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>[OH-].[Na+]>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 79732-BromopyridineHCID 11430Potassium Carbonate

Product 1

HCID 9991408Methyl 4-(pyridin-2-yloxy)benzoateYield 14.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-Bromopyridine (1.00 g), methyl 4-hydroxybenzenecarboxylate (1.92 g) and potassium carbonate (874.9 mg) were stirred at 150° C. for 6 hours. Aqueous 2 N sodium hydroxide solution (50 mL) was added to the reaction liquid, extracted with diethyl ether (100 mL), and the organic layer was washed with water (50 mL) and saturated saline water (50 mL) in that order, and then evaporated under reduced pressure to obtain a pale yellow residue. The resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 8/2) to obtain the entitled compound (208 mg) as a pale yellow solid.

Workup

  1. extractionextracted with diethyl ether (100 mL)
  2. washthe organic layer was washed with water (50 mL) and saturated saline water (50 mL) in that order
  3. customevaporated under reduced pressure
  4. customto obtain a pale yellow residue
  5. customThe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 8/2)

Sources & evidence

ORD record
ord-f3b78fb7fc0d4356a8fe80b0cf89d640
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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