Ethanol → 5-Hydroxyiminomethyl-2-methylnitrobenzene

HRID 1891319Notes

Reaction equation

HRID 1891319 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 962WaterSolvent2×

Procedure

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

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eefeb4d668b94d44be720affa48c8b7f
Source dataset
uspto-grants-2013_08
Patent number
US08507514B2

Reaction notes

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