m-Chloroperbenzoic acid → HCID 22147718, compound

HRID 2227762Notes

Reaction equation

HRID 2227762 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-1a47cd0417f24e6aa56a2909e10efca0
Source dataset
uspto-grants-2002_07
Patent number
US06413991B1

Reaction notes

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