4-Chlorobenzaldehyde → HCID 54558418, compound

HRID 1076297Notes

Reaction equation

HRID 1076297 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]=[C:31]([Cl:33])[CH:30]=[CH:29][C:12]=1[CH2:13][C:14]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:20](=[O:22])[CH3:21])[CH2:15][CH2:16][C:17]([OH:19])=[O:18].[OH-].[Na+]>C(O)C.O>[Cl:10][C:11]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:12]=1[CH2:13][C:14]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:20](=[O:22])[CH:21]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 21540050HCID 21540050, compound

Product 1

HCID 54558418HCID 54558418, 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-(2,4-dichlorobenzyl)-4-phenyl-5-oxohexanoic acid (5.48 g., 0.015 mole) and sodium hydroxide (0.80 g., 0.03 mole) in water (50 ml.). The resulting mixture is heated on a steam bath for 24 hours. Then the reaction solution is cooled to room temperature, diluted with water (200 ml.) and extracted with ether to remove the excess p-chlorobenzaldehyde. The aqueous phase is then acidified with dilute hydrochloric acid (10 ml.), and the sticky solid which precipitates is filtered and air-dried, yield 5.5 g., m.p. 215°-226°C. Recrystallizations from ethanol gives material with m.p. 224.5°-227°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. customthe sticky solid which precipitates
  5. filtrationis filtered
  6. customair-dried
  7. customRecrystallizations from ethanol
  8. customgives material with m.p. 224.5°-227°C.

Sources & evidence

ORD record
ord-562d0c872b1f401687cdffc059c3cc91
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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