Water → HCID 14555668, compound

HRID 1723407Notes

Reaction equation

HRID 1723407 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:6][CH:5]=1.O.NN.O>C(O)COCCO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 14555665HCID 14555665, compound

Product 1

HCID 14555668HCID 14555668, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

To a solution of 3.4 gms KOH in 23 ml diethylene glycol was added 5.4 gms 9(4-chlorophenyl)-7-ketononanoic acid and 3 ml hydrazine hydrate. The resulting mixture was heated at 145° for 1 hour. The mixture was cooled, attached to a water aspirator, and the excess water and hydrazine distilled off. The mixture was then re-heated to 145° for 3 hours and cooled. The oily reaction mixture was diluted with water, acidified with conc. HCl, and the precipitated solid filtered off. Since the NMR showed starting material still present, the solid was dissolved in 25 ml diethylene glycol and 4.1 ml hydrazine hydrate was added. This solution was refluxed for 3 hr, then the water and hydrazine were distilled off under vacuum as before. 5.2 gms KOH was added and the resulting mixture was heated at 160° for 3.5 hours, then cooled to room temperature overnight. It was dissolved in water and acidified with conc. HCl. The precipitated solid was dissolved in 10% KOH solution, washed three times with ether, filtered, acidified with conc. HCl, and placed in the cold overnight. The solid was filtered off, dried and recrystallized from hexanes to give 3.1 gm white solid of m.p. 73°-5° C.

Workup

  1. temperatureThe resulting mixture was heated at 145° for 1 hour
  2. temperatureThe mixture was cooled
  3. distillationthe excess water and hydrazine distilled off
  4. temperatureThe mixture was then re-heated to 145° for 3 hours
  5. temperaturecooled
  6. additionThe oily reaction mixture was diluted with water
  7. filtrationthe precipitated solid filtered off
  8. dissolutionthe solid was dissolved in 25 ml diethylene glycol
  9. addition4.1 ml hydrazine hydrate was added
  10. temperatureThis solution was refluxed for 3 hr
  11. distillationthe water and hydrazine were distilled off under vacuum as before
  12. addition5.2 gms KOH was added
  13. temperaturethe resulting mixture was heated at 160° for 3.5 hours
  14. dissolutionIt was dissolved in water
  15. dissolutionThe precipitated solid was dissolved in 10% KOH solution
  16. washwashed three times with ether
  17. filtrationfiltered
  18. customplaced in the cold overnight
  19. filtrationThe solid was filtered off
  20. customdried
  21. customrecrystallized from hexanes

Sources & evidence

ORD record
ord-5a488cea0ea64d0fae406a29a1aa8cae
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

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