Hydrochloric Acid → HCID 53821538, compound

HRID 1076308Notes

Reaction equation

HRID 1076308 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 (10.5 g., 0.075 mole) in ethanol (30 ml.) is added to a solution of levo-4-(2-chlorobenzyl)-4-phenyl-5-oxohexanoic acid (14.67 g., 0.045 mole) and sodium hydroxide (2.40 g., 0.06 mole) in water (150 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 (30 ml.), and the solid (yellow) which forms after scratching is filtered and air-dried to yield 24.1 g. of material with m.p. 150°-165°C. (sinters at 140°). Several recrystallizations from n-butyl chloride, followed by several recrystallizations from acetonitrile gives a white solid, m.p. 189°-190°C., [α]D25 = -61.5 (in 1% CHCl3).

Workup

  1. temperatureThe resulting mixture is heated on a steam bath for 24 hours
  2. filtrationthe solid (yellow) which forms after scratching is filtered
  3. customair-dried
  4. customto yield 24.1 g
  5. customwith m.p. 150°-165°C. (sinters at 140°)
  6. customSeveral recrystallizations from n-butyl chloride
  7. customfollowed by several recrystallizations from acetonitrile
  8. customgives a white solid, m.p. 189°-190°C., [α]D25 = -61.5 (in 1% CHCl3)

Sources & evidence

ORD record
ord-f02eeda670b44987af5faf65219ff3ea
Source dataset
uspto-grants-1976_05
Patent number
US03956374

Reaction notes

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