Reaction #2336517

Reaction equation

methyl 3-benzyloxypicolinate

3-chloroperoxybenzoic acid

→

methyl 3-benzyloxypicolinate-1-oxide

Yield 94.6%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   ExtractionThe reaction mixture was then extracted with 5% sodium bisulfite solution (100 mL)
2. 2
   DryingAfter drying (MgSO4)
3. 3
   Otherthe solvent was evaporated

Procedure

A solution of methyl 3-benzyloxypicolinate (4.86 g) and 3-chloroperoxybenzoic acid (5.75 g, 60% peracid) in CH2Cl2 (100 mL) was stirred at room temperature for 40 hours. The reaction mixture was then extracted with 5% sodium bisulfite solution (100 mL) then with 0.5N NaOH solution (150 mL). After drying (MgSO4), the solvent was evaporated to give 4.9 g of methyl 3-benzyloxypicolinate-1-oxide as a white solid. Recrystallization from methylcyclohexane/toluene gave a crystalline solid, m.p. 104-106° C.

Source