Benzene → HCID 85965606, compound

HRID 1030452Notes

Reaction equation

HRID 1030452 reaction equation
[C:1]([NH:5][OH:6])([CH3:4])([CH3:3])[CH3:2].[CH:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1.[CH:17]1C=CC=CC=1>CS(O)(=O)=O>[CH2:7]([CH:17]=[N+:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[O-:6])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 312444-MethoxybenzaldehydeHCID 98586N-tert-butylhydroxylamine

Product 1

HCID 85965606HCID 85965606, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidCatalyst

Procedure

A solution of t-butylhydroxylamine (1.0 g, 11 mmole) and p-anisaldehyde (1.5 g, 11 mmole) in 20 mL of benzene was refluxed through a Dean-Stark trap for 18 hours. One drop of methanesulfonic acid was then added and refluxing was continued for an additional two hours. The reaction mixture was then washed with saturated aqueous sodium bicarbonate and the benzene removed under reduced pressure. The residue was recrystallized from petroleum ether. Based on the method of preparation, there was obtained 0.8 g (3.9 mmole) or a 35% yield of the α-anisyl-N-t-butylnitrone having a melting point of 90°-1° C.

Workup

  1. temperaturerefluxing
  2. washThe reaction mixture was then washed with saturated aqueous sodium bicarbonate
  3. customthe benzene removed under reduced pressure
  4. customThe residue was recrystallized from petroleum ether
  5. customBased on the method of preparation
  6. customthere was obtained 0.8 g (3.9 mmole)

Sources & evidence

ORD record
ord-6d8e8fee84234b77aa8f390717c2bd89
Source dataset
uspto-grants-1992_04
Patent number
US05106723

Reaction notes

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