m-Chloroperbenzoic acid → HCID 21490907, compound

HRID 1973892Notes

Reaction equation

HRID 1973892 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH2:9][CH2:10][CH2:11][CH3:12])=[C:4]([Cl:13])[N:3]=1.ClC1C=CC=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH2:9][CH2:10][CH2:11][CH3:12])=[C:4]([Cl:13])[N+:3]=1[O-:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13250416HCID 13250416, compound

Product 1

HCID 21490907HCID 21490907, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

66 g of 2-methyl-4,6-dichloro-5-n-butyl-pyridine are dissolved in 600 ml of methylene chloride and a solution of 66 g of 85% strength m-chloroperbenzoic acid in 600 ml of methylene chloride is added dropwise over the course of 21/2 hours whilst stirring. Thereafter, the mixture is stirred for a further 48 hours at room temperature. The reaction solution is extracted by shaking with aqueous ferrous sulphate solution and with 2 N sodium carbonate solution. The methylene chloride solution is dried and evaporated. 2-Methyl-4,6-dichloro-5-n-butyl-pyridine-N-oxide is thus obtained as the residue. This is taken up in 300 ml of toluene and 82 ml of acetic anhydride are added over the course of 15 minutes whilst stirring. Thereafter the mixture is boiled under reflux for 15 hours. The reaction solution is evaporated. The residue is taken up in ether and extracted by shaking with 2 N sodium carbonate solution. The ether solution is dried and evaporated. After fractionation of the residue, 2-acetoxymethyl- 4,6-dichloro-5-n-butyl-pyridine is obtained.

Workup

  1. stirringThereafter, the mixture is stirred for a further 48 hours at room temperature
  2. extractionThe reaction solution is extracted
  3. stirringby shaking with aqueous ferrous sulphate solution and with 2 N sodium carbonate solution
  4. dry with materialThe methylene chloride solution is dried
  5. customevaporated

Sources & evidence

ORD record
ord-5717bb9e3bce40cfa7912848dd984500
Source dataset
uspto-grants-1976_12
Patent number
US03998955

Reaction notes

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