Hydrochloric Acid → HCID 86733412, compound

HRID 1076302Notes

Reaction equation

HRID 1076302 reaction equation
[CH3:1][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]([CH3:1])=[CH:3][CH:4]=1)[CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77254-MethylbenzaldehydeHCID 14798Sodium HydroxideHCID 103367854-(o-Chlorobenzyl)-4-phenyl-5-oxohexanoic acid

Product 1

HCID 86733412HCID 86733412, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

p-Methylbenzaldehyde (3.00 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 (0.80 g., 0.20 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 collected and air-dried, yield 7.4 g., m.p. 120°-147°C. Recrystallization from methylcyclohexane, followed by recrystallization from n-butyl chloride, yields a white solid with m.p. 166°-168.5°C.

Workup

  1. temperatureThe resulting mixture is heated on a steam bath for 24 hours
  2. customthe sticky solid which forms after scratching is collected
  3. customair-dried
  4. customRecrystallization from methylcyclohexane
  5. customfollowed by recrystallization from n-butyl chloride
  6. customyields a white solid with m.p. 166°-168.5°C.

Sources & evidence

ORD record
ord-a44b7af0659843a989fbfbccac2c9b14
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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