Sodium Acetate → HCID 12874007, compound

HRID 443881Notes

Reaction equation

HRID 443881 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:5]([N+:17]([O-])=O)=[CH:4][C:3]=1Cl.C([O-])(=O)C.[Na+].[H][H]>[Pd].[Cl-].[Zn+2].[Cl-].CO>[CH2:8]([C:6]1[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=1[NH2:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 3

HCID 517045Sodium AcetateHCID 20446969HCID 20446969, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12874007HCID 12874007, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 120 parts of 1,2-dichloro-4-nitro-5-nonylbenzene, 2 parts of zinc chloride solution, 83 parts of sodium acetate and 480 parts of methanol is hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is dissolved in water and the solution is alkalized with ammonium hydroxide. The product is extracted with 2,2'-oxybispropane. The extract is washed with water, dried, filtered and evaporated. The residue is distilled, yielding 59 parts of 2-nonylbenzenamine; bp. 131°-132° C. at 0.2 mm pressure.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. dissolutionThe residue is dissolved in water
  4. extractionThe product is extracted with 2,2'-oxybispropane
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. distillationThe residue is distilled

Sources & evidence

ORD record
ord-47beefb3f4864f21843c59adff238d37
Source dataset
uspto-grants-1981_04
Patent number
US04262004

Reaction notes

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