3-Chlorobenzaldehyde → HCID 86733413, compound

HRID 1076304Notes

Reaction equation

HRID 1076304 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[Cl: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>[Cl: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:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=1)[CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 103367854-(o-Chlorobenzyl)-4-phenyl-5-oxohexanoic acid

Product 1

HCID 86733413HCID 86733413, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

m-Chlorobenzaldehyde (3.5 g., 0.025 mole) in ethanol (10 ml.) is added to a solution of levo-4-(o-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 (300 ml.), and extracted with ether to remove the excess m-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 off-white solid that precipitates is filtered and air-dried. Several recrystallizations from n-butyl chloride yields 3.15 g. of material with m.p. 170°-172°C.

Workup

  1. temperatureThe resulting mixture is heated on a steam bath for 24 hours
  2. extractionextracted with ether
  3. customto remove the excess m-chlorobenzaldehyde
  4. temperatureby warming
  5. temperatureThe solution is cooled in an ice bath
  6. customthe off-white solid that precipitates
  7. filtrationis filtered
  8. customair-dried
  9. customSeveral recrystallizations from n-butyl chloride
  10. customyields 3.15 g

Sources & evidence

ORD record
ord-6ace7e5911e84186868a69baa4817ac5
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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