4-Chlorobenzaldehyde → HCID 53674873, compound

HRID 1076303Notes

Reaction equation

HRID 1076303 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:32]=[CH:31][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>[Br:10][C:11]1[CH:32]=[CH:31][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])[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 21540047HCID 21540047, compound

Product 1

HCID 53674873HCID 53674873, 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-bromobenzyl)-4-phenyl-5-oxohexanoic acid (3.0 g., 0.006 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, acidified with dilute hydrochloric acid (10 ml.), and the yellowish solid which precipitates is collected and air-dried to yield 3.5 g. Recrystallization from ethanol gives material with m.p. 210°-213.5°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
  6. customthe yellowish solid which precipitates
  7. customis collected
  8. customair-dried
  9. customto yield 3.5 g
  10. customRecrystallization from ethanol
  11. customgives material with m.p. 210°-213.5°C.

Sources & evidence

ORD record
ord-5d8ef66d7a6842419e317d4f80629eb9
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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