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

HRID 1003656Notes

Reaction equation

HRID 1003656 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-b5f51e8c0d8843f2820b2fa8b38d6049
Source dataset
uspto-grants-2000_04
Patent number
US06046232

Reaction notes

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