Sodium Hydroxide → HCID 72770457, compound

HRID 394836Notes

Reaction equation

HRID 394836 reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([C:7]([Cl: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>[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([C:7]([Cl:10])=[CH:8][CH:9]=1)[CH:5]=[N:17][OH:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 11217711HCID 11217711, compound

Product 1

HCID 72770457HCID 72770457, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

198 g (0.975 mol) of 93% pure 3,6-dichloro-2-methylbenzaldehyde and 416.2 g (0.634 mol) of a 25% strength aqueous solution of hydroxylamine sulfate are mixed in 1.5 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, and the phases are then separated at 80° C. The organic phase is washed once with 250 ml of water. The organic phase is concentrated and the residue is recrystallized from cyclohexane. This gives 165.4 g of the aldoxime (83.3% of theory). 1H-NMR: (DMSO-D6): 2.4 ppm (s, 3H, Me), 7.4 ppm (d, 1H, arom-H), 7.5 ppm (d, 1H, arom-H), 8.3 ppm (s, 1H, NH), 11.7 ppm (s, 1H, OH).

Workup

  1. waitis continued for 1 h
  2. customthe phases are then separated at 80° C
  3. washThe organic phase is washed once with 250 ml of water
  4. concentrationThe organic phase is concentrated
  5. customthe residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-d3a02abe50e042ab8d0005726387ab42
Source dataset
uspto-grants-2003_08
Patent number
US06603017B2

Reaction notes

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