4-Chlorobenzaldehyde → HCID 53808416, compound

HRID 1076305Notes

Reaction equation

HRID 1076305 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:32]=[CH:31][C:14]([CH2:15][C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:22](=[O:24])[CH3:23])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=1.[OH-].[Na+]>C(O)C.O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][C:16]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:22](=[O:24])[CH:23]=[CH:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 21540032HCID 21540032, compound

Product 1

HCID 53808416HCID 53808416, 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-(p-chlorobenzyl)-4-phenyl-5-oxohexanoic acid (3.0 g., .009 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 (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 yellowish solid which precipitates is collected and air-dried to yield 3.1 g., m.p. 65°-145°C. Several recrystallizations from n-butyl chloride yields a material with m.p. 176°-178.5°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 yellowish solid which precipitates
  7. customis collected
  8. customair-dried
  9. customto yield 3.1 g
  10. customSeveral recrystallizations from n-butyl chloride
  11. customyields a material with m.p. 176°-178.5°C.

Sources & evidence

ORD record
ord-ad93ef5fc94544ec8937182cfd157212
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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