Hydrochloric Acid → HCID 14555669, compound

HRID 1723405Notes

Reaction equation

HRID 1723405 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:5][CH:4]=1.O.NN.Cl>C(O)COCCO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 14555666HCID 14555666, compound

Product 1

HCID 14555669HCID 14555669, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8117Diethylene GlycolSolvent

Procedure

To a stirring solution of 7.5 gms 9(4-methoxyphenyl)-7-ketononanoic acid in 35 ml diethylene glycol was added 5.1 ml hydrazine hydrate. The mixture was heated to 120° for 4 hrs, cooled to room temperature, connected to a water aspirator, and gently heated to 120° to remove excess water and hydrazine. The reaction mixture was cooled to 70°, 7.2 gm KOH was added, and the mixture was heated up to 220° C. where it was kept for 5 hr, then cooled. The cooled reaction mass was dissolved in 120 ml hot water, acidified with conc. HCl, and 3× extracted with CHCl3. The combined organic phases were dried over MgSO4, filtered, and the solvent was evaporated in vacuo. Attempts to crystallize the product failed, so it was vacuum sublimed twice, dissolved in 300 ml chloroform, filtered through silica gel, and the solvent evaporated to give 38% product, a white solid of m.p. 41°-3° C.

Workup

  1. temperatureThe mixture was heated to 120° for 4 hrs
  2. temperaturegently heated to 120°
  3. customto remove excess water and hydrazine
  4. temperatureThe reaction mixture was cooled to 70°
  5. addition7.2 gm KOH was added
  6. temperaturethe mixture was heated up to 220° C. where it
  7. temperaturecooled
  8. customThe cooled reaction mass
  9. extractionextracted with CHCl3
  10. dry with materialThe combined organic phases were dried over MgSO4
  11. filtrationfiltered
  12. customthe solvent was evaporated in vacuo
  13. customto crystallize the product
  14. dissolutiondissolved in 300 ml chloroform
  15. filtrationfiltered through silica gel
  16. customthe solvent evaporated

Sources & evidence

ORD record
ord-6c7c9aea9b8c407d906971b0fba53ff9
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

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