Hydrochloric Acid → HCID 20304491, compound

HRID 1732684Notes

Reaction equation

HRID 1732684 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17](=[O:26])[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])=[CH:13]N(C)C)=[CH:8][CH:7]=1)([OH:3])=[O:2].Cl.[OH-:28].[K+]>>[OH:19][C:18]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17](=[O:26])[C:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])=[CH:7][CH:8]=2)=[CH:13][O:28]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54263071HCID 54263071, compound

Product 1

HCID 20304491HCID 20304491, compoundYield 93%

Procedure

A solution of 3.95 g of 2-[4-(2-carboxyethyl)phenyl]-1-dimethylamino-4-phenyl-1-butene-3,4-dione in 100 ml of 2% potassium hydroxide solution was stirred at room temperature for 31/2 hrs. The reaction mixture was poured onto 300 ml of ice-water, acidified with 100 ml of 1 N hydrochloric acid and extracted with methylene chloride. The organic extract was washed with water, dried, filtered, and evaporated. Recrystallization of a sample of the residue from methylene chloride-petroleum ether gave 2-hydroxy-2-phenyl-4-[4-(2-carboxyethyl)phenyl]-3(2H)-furanone as colorless crystals, m.p. 89°-95° dec., after drying at 50° C.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe organic extract
  3. washwas washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customRecrystallization of a sample of the residue from methylene chloride-petroleum ether

Sources & evidence

ORD record
ord-88017089e7d14640858f92e709d089f3
Source dataset
uspto-grants-1980_12
Patent number
US04238589

Reaction notes

Loading…