m-Chloroperbenzoic acid → HCID 22147718, compound

HRID 2119825Notes

Reaction equation

HRID 2119825 reaction equation
[CH3:1][C:2]([N+:20]([O-:22])=[O:21])([CH3:19])[CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12](C=O)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.ClC1C=C(C=CC=1)C(OO)=[O:28]>C(Cl)(Cl)Cl>[CH3:1][C:2]([N+:20]([O-:22])=[O:21])([CH3:19])[CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([OH:28])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22147825HCID 22147825, compound

Product 1

HCID 22147718HCID 22147718, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-(4-(2-Methyl-2-nitropropyl)phenoxy)benzaldehyde (6.00 g, 20 mmol) was dissolved in chloroform (500 mL). m-Chloroperoxy-benzoic acid (10.0 g, 58 mmol) was added in small portions at RT. After stirring for 1 hour, the mixture was concentrated in vacuo and MeOH (300 mL) added followed by the dropwise addition of conc. HCl (5 mL). This mixture was stirred for 3 hours at RT and then concentrated in vacuo. Chromatography over silica gel (MeOH/CHCl3) allowed for the isolation of 3.20 g (55%) of the desired product. MS(FD+): 287.2

Workup

  1. concentrationthe mixture was concentrated in vacuo and MeOH (300 mL)
  2. additionadded
  3. additionfollowed by the dropwise addition of conc. HCl (5 mL)
  4. stirringThis mixture was stirred for 3 hours at RT
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f458c3bf0a86498cb16b2ca0112437bb
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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