Sodium Hydroxide → 3,3'-Diisobutoxybenzidine

HRID 704481Notes

Reaction equation

HRID 704481 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH:12]([CH3:14])[CH3:13])([O-])=O.[OH-:15].[Na+]>[Fe].[Zn].O.[O-2].[Zn+2].O>[CH2:11]([O:10][C:5]1[CH:6]=[C:7]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[C:5]([O:15][CH2:11][CH:12]([CH3:14])[CH3:13])[CH:6]=2)[CH:8]=[CH:9][C:4]=1[NH2:1])[CH:12]([CH3:14])[CH3:13]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 122152032-(2-Methylpropoxy)-1-nitrobenzene

Product 1

HCID 137421523,3'-Diisobutoxybenzidine

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 23994ZincCatalyst2×HCID 22593153ZINC;oxygen(2-);hydrateCatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

An iron apparatus equipped with horseshoe stirrer and heating and cooling means is charged with 293 g of o-nitro-isobutoxybenzene, 395 g of solvent naphtha and 220 g of zinc dust. The reaction mixture is heated with stirring to 80° C., and first 24 g of 50% strength sodium hydroxide solution and then 21 g of water are added with temporary cooling. To complete the reduction, stirring is continued at 80° C. with the addition of further zinc dust a little at a time (in total 53 g) until a spot test with the reaction solution shows a colorless runoff. By further addition of water the zinc oxide hydrate is then grained. The zinc oxide hydrate is then separated by filtration from the organic phase containing the 2,2'-diisobutoxyhydrazobenzene and as byproduct 1-isobutoxy-2-aminobenzene. After extraction of the byproduct with dilute hydrochloric acid the organic phase is added dropwise at 15°-20° C. to hydrochloric acid and stirring is continued at 25° C. until the rearrangement reaction has ended (test: hydrazo compound no longer detectable). The crude product is purified by filtration, dissolving in hot water and clarification of the solution with Carboraffin. Precipitation with concentrated hydrochloric acid gives 106 g of 3,3'-diisobutoxybenzidine dichlorohydrate having a diazotization value of 96%, melting point 270° C.

Workup

  1. temperatureheating
  2. temperaturecooling means
  3. temperatureThe reaction mixture is heated
  4. stirringstirring
  5. customThe zinc oxide hydrate is then separated by filtration from the organic phase
  6. additioncontaining the 2,2'-diisobutoxyhydrazobenzene
  7. extractionAfter extraction of the byproduct with dilute hydrochloric acid the organic phase
  8. additionis added dropwise at 15°-20° C. to hydrochloric acid
  9. stirringstirring
  10. customis continued at 25° C. until the rearrangement reaction
  11. filtrationThe crude product is purified by filtration
  12. dissolutiondissolving in hot water
  13. customPrecipitation with concentrated hydrochloric acid

Sources & evidence

ORD record
ord-cf565c0af5884be5b465b19d9a6b8114
Source dataset
uspto-grants-1991_01
Patent number
US04987258

Reaction notes

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