Pyruvic Acid → 2,2-Bis(4-pyrrolidinophenyl)propionic acid

HRID 1199108Notes

Reaction equation

HRID 1199108 reaction equation
S(=O)(=O)(O)O.[C:6]1([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:17]([OH:22])(=[O:21])[C:18]([CH3:20])=O.[OH-].[Na+]>O>[N:12]1([C:6]2[CH:11]=[CH:10][C:9]([C:18]([C:9]3[CH:8]=[CH:7][C:6]([N:12]4[CH2:13][CH2:14][CH2:15][CH2:16]4)=[CH:11][CH:10]=3)([CH3:20])[C:17]([OH:22])=[O:21])=[CH:8][CH:7]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 1060Pyruvic AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 777261-Phenylpyrrolidine

Product 1

HCID 142278762,2-Bis(4-pyrrolidinophenyl)propionic acidYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 40 ml of 20% aqueous solution of sulfuric acid was dissolved 20 g of N-phenylpyrrolidine. To the solution was added 7.2 g of pyruvic acid and the mixture was heated with reflux for 16 hours. The reaction mixture was, after cooled, diluted with 300 ml of water and adjusted to pH 6 with addition of 20% aqueous solution of sodium hydroxide. The precipitated crystal was collected by filtration. The crystal was recrystallized from benzene to obtain 18.5 g (yielded 75%) of 2,2-bis(4-pyrrolidinophenyl)propionic acid as white crystal, having a melting point of 174°~176° C.

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 16 hours
  3. temperatureafter cooled
  4. filtrationThe precipitated crystal was collected by filtration
  5. customThe crystal was recrystallized from benzene

Sources & evidence

ORD record
ord-9dcd38d4461449659db38d131e4f1a7b
Source dataset
uspto-grants-1990_02
Patent number
US04898941

Reaction notes

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