Hydrochloric Acid → 2-hydroxy-2-phenyl-4-(4-carboxyphenyl)-3(2H)-furanone

HRID 918094Notes

Reaction equation

HRID 918094 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:15](=[O:24])[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])=[CH:11]N(C)C)=[CH:6][CH:5]=1)([OH:3])=[O:2].Cl.[OH-:26].[K+]>>[OH:17][C:16]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](=[O:24])[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=2)=[CH:11][O:26]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 540610692-(4-Carboxyphenyl)-1-dimethylamino-4-phenyl-1-butene-3,4-dione

Product 1

HCID 203044972-hydroxy-2-phenyl-4-(4-carboxyphenyl)-3(2H)-furanoneYield 71%

Procedure

A solution of 3.23 g of 2-(4-carboxyphenyl)-1-dimethylamino-4-phenyl-1-butene-3,4-dione in 100 ml of 2% potassium hydroxide solution was stirred at room temperature for 5 hrs. The reaction mixture was poured onto 300 ml of ice-water and acidified with 100 ml of 1N hydrochloric acid. The precipitate was collected, washed with water and then dissolved in 300 ml of ether. The solution was dried over anhydrous sodium sulfate. The drying agent was collected and the filtrate was evaporated. Recrystallization from ether gave 2.12 g (71%) of 2-hydroxy-2-phenyl-4-(4-carboxyphenyl)-3(2H)-furanone, m.p. 294°-299°C. dec.

Workup

  1. customThe precipitate was collected
  2. washwashed with water
  3. dissolutiondissolved in 300 ml of ether
  4. dry with materialThe solution was dried over anhydrous sodium sulfate
  5. customThe drying agent was collected
  6. customthe filtrate was evaporated
  7. customRecrystallization from ether

Sources & evidence

ORD record
ord-63eab27995654ed69866ec52ea479e07
Source dataset
uspto-grants-1976_07
Patent number
US03969373

Reaction notes

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