2,6-Dichlorobenzaldehyde → HCID 86733414, compound

HRID 1076307Notes

Reaction equation

HRID 1076307 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[Cl:11][C:12]1[CH:33]=[CH:32][CH:31]=[CH:30][C:13]=1[CH2:14][C:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:21](=[O:23])[CH3:22])[CH2:16][CH2:17][C:18]([OH:20])=[O:19].[OH-].[Na+]>C(O)C.O>[Cl:11][C:12]1[CH:33]=[CH:32][CH:31]=[CH:30][C:13]=1[CH2:14][C:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:21](=[O:23])[CH:22]=[CH:4][C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10])[CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 103367854-(o-Chlorobenzyl)-4-phenyl-5-oxohexanoic acid

Product 1

HCID 86733414HCID 86733414, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

2,6-Dichlorobenzaldehyde (4.38 g., 0.025 mole) in ethanol (10 ml.) is added to a solution of levo-4-(o-chlorobenzyl)-4-phenyl-5-oxohexanoic acid (4.89 g., 0.015 mole) and sodium hydroxide (0.8 g., 0.02 mole) in water (50 ml.). The resulting mixture is heated on a steam bath for 24 hours. The reaction solution is cooled to room temperature, diluted with water (200 ml.) and extracted with ether to remove the excess 2,6-dichlorobenzaldehyde. Ether is expelled from the aqueous phase by warming. The solution is cooled to room temperature, acidified with dilute hydrochloric acid (10 ml.), and the gummy oil which separates is extracted into ether. The ether extract is washed with brine solution, and dried (Na2SO4). Removal of the ether in vacuo, yields a yellowish residue which after recrystallization from a mixture of n-butyl chloride and petroleum ether (30°-60°C.) gives a white material, 1.75 g., m.p. 140.5°-143°C.

Workup

  1. temperatureThe resulting mixture is heated on a steam bath for 24 hours
  2. extractionextracted with ether
  3. customto remove the excess 2,6-dichlorobenzaldehyde
  4. temperatureby warming
  5. temperatureThe solution is cooled to room temperature
  6. extractionthe gummy oil which separates is extracted into ether
  7. extractionThe ether extract
  8. washis washed with brine solution
  9. dry with materialdried (Na2SO4)
  10. customRemoval of the ether in vacuo
  11. customyields a yellowish residue which
  12. customafter recrystallization
  13. additionfrom a mixture of n-butyl chloride and petroleum ether (30°-60°C.)
  14. customgives a white material, 1.75 g

Sources & evidence

ORD record
ord-bdf7964aaa304815972b687dabce6c97
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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