Hydrochloric Acid → HCID 20304491, compound

HRID 442419Notes

Reaction equation

HRID 442419 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 icewater, acidified with 100 ml of 1N 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. additionThe reaction mixture was poured onto 300 ml of icewater
  2. extractionextracted with methylene chloride
  3. extractionThe organic extract
  4. washwas washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customRecrystallization of a sample of the residue from methylene chloride-petroleum ether

Sources & evidence

ORD record
ord-71232c4fcde84a5384faf0e340967f7a
Source dataset
uspto-grants-1977_08
Patent number
US04045487

Reaction notes

Loading…