m-Chloroperbenzoic acid → HCID 23150273, compound

HRID 657655Notes

Reaction equation

HRID 657655 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N+:15]([O-:26])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23150278HCID 23150278, compound

Product 1

HCID 23150273HCID 23150273, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-[4-(3-chloropropoxy)phenyl]pyridine (1.22 g) and metachloroperbenzoic acid (1.82 g) in chloroform (25 mL) is stirred at room temperature for four hours, then concentrated under reduced pressure and purified by column chromatography over silica gel using a gradient dichloromethane/methanol from 100/0 to 95/5. Fractions containing the expected product are pooled and concentrated under reduced pressure to give 1.09 g of 4-[4-(3-chloropropoxy)phenyl]pyridine 1-oxide as a pale yellow solid used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by column chromatography over silica gel using a gradient dichloromethane/methanol from 100/0 to 95/5
  3. additionFractions containing the expected product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93738364d72e4f458cbc077f8a166de2
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

Loading…