4-Chlorobenzaldehyde → HCID 54000748, compound

HRID 1076298Notes

Reaction equation

HRID 1076298 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][C:32]=1[Cl:33])[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][C:32]=1[Cl:33])[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 21540015HCID 21540015, compound

Product 1

HCID 54000748HCID 54000748, 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-(3,4-dichlorobenzyl)-4-phenyl-5-oxohexanoic acid (5.48 g., 0.015 mole) and sodium hydroxide (0.80 g., 0.02 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 (250 ml.), and extracted with ether to remove the excess p-chlorobenzaldehyde. The aqueous phase is then acidified with dilute hydrochloric acid (15 ml.). The organic material which separates is extracted into ether, washed with saturated brine, and dried over Na2SO4. The ether is removed in vacuo, and trituration of the residue with ethanol (25 ml.) produces 1.6 g. of solid. Recrystallization from butyl chloride gives material with m.p. 155°-156.5°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. extractionThe organic material which separates is extracted into ether
  5. washwashed with saturated brine
  6. dry with materialdried over Na2SO4
  7. customThe ether is removed in vacuo, and trituration of the residue with ethanol (25 ml.)
  8. customproduces 1.6 g
  9. customRecrystallization from butyl chloride
  10. customgives material with m.p. 155°-156.5°C.

Sources & evidence

ORD record
ord-a67aa23f94c9456ab612fe761888e871
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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