Sodium Hydroxide → 3,6-Dibromo-2-methylbenzaldoxime

HRID 394837Notes

Reaction equation

HRID 394837 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([C:7]([Br:10])=[CH:8][CH:9]=1)[CH:5]=O.S(O)(O)(=O)=O.[NH2:17][OH:18].[OH-].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([C:7]([Br:10])=[CH:8][CH:9]=1)[CH:5]=[N:17][OH:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 121004293,6-Dibromo-2-methylbenzaldehyde

Product 1

HCID 865861873,6-Dibromo-2-methylbenzaldoxime

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

10 g (0.42 mol) of 3,6-dibromo-2-methylbenzaldehyde and 178.5 g (0.272 mol) of a 25% strength aqueous solution of hydroxylamine sulfate are mixed in 1.2 l of toluene and heated at 80° C. Over a period of 2 h, 109.2 g (1.36 mol) of 50% strength NaOH are then added dropwise such that the pH is between 3 and 5. Stirring at 80° C. is continued for 1 h, the mixture is stirred at room temperature overnight and the phases are then separated at 80° C. The organic phase is washed once with 350 ml of water. The organic phase is concentrated and the residue is recrystallized from cyclohexane. This gives 113.9 g (93% of theory) of the aldoxime.

Workup

  1. waitis continued for 1 h
  2. stirringthe mixture is stirred at room temperature overnight
  3. customthe phases are then separated at 80° C
  4. washThe organic phase is washed once with 350 ml of water
  5. concentrationThe organic phase is concentrated
  6. customthe residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-70b79f78093c4f2597a846ccebc27aa0
Source dataset
uspto-grants-2003_08
Patent number
US06603017B2

Reaction notes

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