m-Chloroperbenzoic acid → HCID 15239991, compound

HRID 277144Notes

Reaction equation

HRID 277144 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:15]([O:17][CH3:18])=[O:16])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:24]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[N+:11]([O-:24])[C:10]=1[C:15]([O:17][CH3:18])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22175081Methyl 3-benzyloxypicolinate

Product 1

HCID 15239991HCID 15239991, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. extractionThe reaction mixture was then extracted with 5% sodium bisulfite solution (100 mL)
  2. dry with materialAfter drying (MgSO4)
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-aff5e518ff49474ca3e6c8c87f10bdbf
Source dataset
uspto-grants-2002_03
Patent number
US06355660B1

Reaction notes

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