Hydrochloric Acid → HCID 86733411, compound

HRID 1076301Notes

Reaction equation

HRID 1076301 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:33]=[CH:32][CH:31]=[CH:30][C:13]=1[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+].Cl>C(O)C.O>[Cl:11][C:12]1[CH:33]=[CH:32][CH:31]=[CH:30][C:13]=1[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:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312444-MethoxybenzaldehydeHCID 103367854-(o-Chlorobenzyl)-4-phenyl-5-oxohexanoic acid

Product 1

HCID 86733411HCID 86733411, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

p-Methoxybenzaldehyde (3.4 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., 0.02 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 sticky solid which forms after scratching is filtered and air-dried. Recrystallization from n-butyl chloride yields 3.2 g., m.p. 152°-157°C. An additional recrystallization from n-butyl chloride yields material with m.p. 159°-160.5°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. customRecrystallization from n-butyl chloride
  5. customyields 3.2 g
  6. customAn additional recrystallization from n-butyl chloride
  7. customyields material with m.p. 159°-160.5°C.

Sources & evidence

ORD record
ord-4cca31912c5b4cd5b77ec0d351921e41
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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