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Hydrochloric Acid → HCID 53821538, compound

HRID 1076299
Notes
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Reaction equation

HRID 1076299 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][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+].Cl>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: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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 103367854-(o-Chlorobenzyl)-4-phenyl-5-oxohexanoic acid

Product 1

HCID 53821538HCID 53821538, compound

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

p-Chlorobenzaldehyde (3.5 g., 0.025 mole) in ethanol (10 ml.) is added to a solution of 4-(o-chlorobenzyl)-4-phenyl-5-oxohexanoic acid (4.89 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. The reaction solution is cooled to room temperature, acidified with dilute hydrochloric acid (10 ml.), and the sticky solid which forms after scratching is filtered and air-dried, yield 7.0 g., m.p. 190°-213°C. Several recrystallizations from nitromethane, followed by a final recrystallization from acetonitrile, gives a light yellow solid with m.p. 223°-227°C.

Workup

  1. temperatureThe resulting mixture is heated on a steam bath for 24 hours
  2. filtrationthe sticky solid which forms after scratching is filtered
  3. customair-dried
  4. customSeveral recrystallizations from nitromethane
  5. customrecrystallization from acetonitrile
  6. customgives a light yellow solid with m.p. 223°-227°C.

Sources & evidence

ORD record
ord-62ef3cb85e444444b39f932dc376dc59
Source dataset
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03956374

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes