Ethanol → 5-Hydroxyiminomethyl-2-methylnitrobenzene

HRID 1627002Notes

Reaction equation

HRID 1627002 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].Cl.[NH2:14][OH:15].C(O)C.C([O-])(=O)C.[Na+]>O>[OH:15][N:14]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 17989983-Nitro-p-tolualdehyde

Product 1

HCID 536283185-Hydroxyiminomethyl-2-methylnitrobenzeneYield 84.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-methyl-3-nitrobenzaldehyde (3.00 g), hydroxylamine hydrochloride (1.64 g), ethanol (30 mL) and water (15 ml) was added sodium acetate (2.24 g) at room temperature, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 5-hydroxyiminomethyl-2-methylnitrobenzene (2.77 g).

Workup

  1. extractionThe reaction mixture was extracted with water and ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c62a1f3c11d944a8b0aee0448949edaa
Source dataset
uspto-grants-2014_07
Patent number
US08785485B2

Reaction notes

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