p-(Hexyloxy)benzaldehyde → alpha-(4-Hexyloxyphenyl)-N-tert-butylnitrone

HRID 2305817Notes

Reaction equation

HRID 2305817 reaction equation
[CH2:1]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:16]([NH:20][OH:21])([CH3:19])([CH3:18])[CH3:17]>C1C=CC=CC=1>[CH2:1]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[N+:20]([C:16]([CH3:19])([CH3:18])[CH3:17])[O-:21])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 79816p-(Hexyloxy)benzaldehydeHCID 98586N-tert-butylhydroxylamine

Product 1

HCID 86587918alpha-(4-Hexyloxyphenyl)-N-tert-butylnitroneYield 55.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-hexyloxybenzaldehyde (3.83 g, 18.6 mmol) in 120 mL of benzene was refluxed with N-tert-butylhydroxylamine (3.32 g, 37.2 mmol) for 18 hours. The reaction mixture was then concentrated by rotary evaporation and the resulting residue was purified by silica gel column chromatography using 50:50 ethyl acetate/hexane to afford the title compound (2.88 g, 55.8% yield) as a solid, m.p. 69.0° C.

Workup

  1. concentrationThe reaction mixture was then concentrated by rotary evaporation
  2. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bd99db3584f74cf38bc4d763dac2fb12
Source dataset
uspto-grants-2002_08
Patent number
US06441032B1

Reaction notes

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