Hydrochloric Acid → HCID 53821538, compound

HRID 1076300Notes

Reaction equation

HRID 1076300 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]

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 702EthanolSolventHCID 962WaterSolvent

Procedure

p-Chlorobenzaldehyde (3.5 g., 0.025 mole) in ethanol (10 ml.) is added to a solution of dextro-4-(o-chlorobenzyl)-4-phenyl-5-oxohexanoic acid (4.89 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. The reaction solution is cooled to room temperature, acidified with dilute hydrochloric acid (10 ml.), and the yellow solid which precipitates is collected and air-dried, yield 7.1 g., m.p. 125°-157°C. Several recrystallizations from n-butyl chloride yields a white solid with m.p. 184.5°-187°C.

Workup

  1. temperatureThe resulting mixture is heated on a steam bath for 24 hours
  2. customthe yellow solid which precipitates
  3. customis collected
  4. customair-dried
  5. customSeveral recrystallizations from n-butyl chloride
  6. customyields a white solid with m.p. 184.5°-187°C.

Sources & evidence

ORD record
ord-5470bd7a717346cb8bb65d7ceccc5cb0
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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