Benzaldehyde, 2-ethoxy- → alpha-(2-Ethoxyphenyl)-N-tert-butylnitrone

HRID 2305779Notes

Reaction equation

HRID 2305779 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)[CH3:2].[C:12]([NH:16][OH:17])([CH3:15])([CH3:14])[CH3:13]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[N+:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[O-:17])[CH3:2]

Participants

4

Reactant 2

HCID 11950Benzaldehyde, 2-ethoxy-HCID 98586N-tert-butylhydroxylamine

Product 1

HCID 85054545alpha-(2-Ethoxyphenyl)-N-tert-butylnitroneYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Ethoxybenzaldehyde (12.0 g, 79.90 mmol) and N-tert-butylhydroxylamine (10.69 g, 119.86 mmol) were mixed in chloroform with molecular sieves (50 g, 4A) and silica gel (10 g). The mixture was sealed under argon gas and stirred for 70 h at room temperature. The mixture was then filtered and the solid washed with ethyl acetate and the combined solution was rotary evaporated. Pentane (50 mL) was added to the liquid residue and isolation of the resulting solid afforded 13.79 g (78.0% yield) of the title compound as white crystals, m.p. 58.3+ C. (Rf=0.55 on a silica gel plate using ethyl acetate as the eluant).

Workup

  1. customThe mixture was sealed under argon gas
  2. filtrationThe mixture was then filtered
  3. washthe solid washed with ethyl acetate
  4. additionPentane (50 mL) was added to the liquid residue and isolation of the resulting solid

Sources & evidence

ORD record
ord-11b45f8ceea94f5cb8b60a5eb9327237
Source dataset
uspto-grants-2002_08
Patent number
US06441032B1

Reaction notes

Loading…