4-Chlorobenzaldehyde → HCID 53654255, compound

HRID 1076310Notes

Reaction equation

HRID 1076310 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:34]=[CH:33][CH:32]=[CH:31][C:12]=1[CH:13]=[CH:14][CH2:15][C:16]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:22](=[O:24])[CH3:23])[CH2:17][CH2:18][C:19]([OH:21])=[O:20].[OH-].[Na+]>C(O)C.O>[Cl:10][C:11]1[CH:34]=[CH:33][CH:32]=[CH:31][C:12]=1[CH:13]=[CH:14][CH2:15][C:16]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:22](=[O:24])[CH:23]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:17][CH2:18][C:19]([OH:21])=[O:20]

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 53835042HCID 53835042, compound

Product 1

HCID 53654255HCID 53654255, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

p-Chlorobenzaldehyde (2.81 g., 0.02 mole) in ethanol (10 ml.) is added to a solution of 4-(o-chlorocinnamyl)-4-phenyl-5-oxohexanoic acid (3.57 g., 0.01 mole) and sodium hydroxide (0.56 g., 0.014 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 (250 ml.), and extracted with ether to remove the excess p-chlorobenzaldehyde. The aqueous phase is acidified with dilute hydrochloric acid (10 ml.), and the gum that separates out is extracted into ether. The ether extract is washed with brine solution, and dried over anhydrous Na2SO4. Filtration and removal of the ether in vacuo gives a viscous yellow residue, which upon trituration with petroleum ether (30°-60°C., 150 ml.) yields 4.3 g. of material, m.p. 90°-125°C. (cloudy). Recrystallization from n-butyl chloride, followed by ethanol, produces a material with m.p. 143°-146°C.

Workup

  1. temperatureThe resulting mixture is heated on a steam bath for 24 hours
  2. extractionextracted with ether
  3. customto remove the excess p-chlorobenzaldehyde
  4. extractionthe gum that separates out is extracted into ether
  5. extractionThe ether extract
  6. washis washed with brine solution
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationFiltration and removal of the ether in vacuo
  9. customgives a viscous yellow residue, which upon trituration with petroleum ether (30°-60°C., 150 ml.)
  10. customyields 4.3 g
  11. customRecrystallization from n-butyl chloride
  12. customproduces a material with m.p. 143°-146°C.

Sources & evidence

ORD record
ord-d307b399c37c48708a31a6d41bdf52b1
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

Loading…