4-Chlorobenzaldehyde → HCID 54198477, compound

HRID 1076306Notes

Reaction equation

HRID 1076306 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:12]=[C:13]([CH:30]=[CH:31][CH:32]=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:10][C:11]1[CH:12]=[C:13]([CH:30]=[CH:31][CH:32]=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:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 21540028HCID 21540028, compound

Product 1

HCID 54198477HCID 54198477, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

p-Chlorobenzaldehyde (3.5 g., 0.025 mole) in ethanol (10 ml.) is added to a solution of 4-(m-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 p-chlorobenzaldehyde. Ether is expelled from the aqueous phase by warming. The solution is cooled in an ice bath, acidified with dilute hydrochloric acid (10 ml.), and the white solid which precipitates is collected and air-dried to yield 5.05 g., m.p. 65°-130°C. Several recrystallizations from n-butyl chloride and petroleum ether (30°-60°C.) give a material with m.p. 137°-139°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. temperatureby warming
  5. temperatureThe solution is cooled in an ice bath
  6. customthe white solid which precipitates
  7. customis collected
  8. customair-dried
  9. customto yield 5.05 g
  10. customSeveral recrystallizations from n-butyl chloride and petroleum ether (30°-60°C.)
  11. customgive a material with m.p. 137°-139°C.

Sources & evidence

ORD record
ord-76f8d887cf254f628a2d4d23f401992b
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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