Hydrochloric Acid → 2-((4-Oxo-3-phenyl-4H-1-benzopyran-7-yl)oxy)propanoic acid

HRID 236343

Reaction equation

HRID 236343 reaction equation
C([O:3][C:4]([CH:6]([O:8][C:9]1[CH:25]=[CH:24][C:12]2[C:13](=[O:23])[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][O:16][C:11]=2[CH:10]=1)[CH3:7])=[O:5])C.O1CCOCC1.Cl>O>[OH:5][C:4]([CH:6]([O:8][C:9]1[CH:25]=[CH:24][C:12]2[C:13](=[O:23])[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][O:16][C:11]=2[CH:10]=1)[CH3:7])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 3579826Ethyl 2-[(4-oxo-3-phenyl-4H-chromen-7-yl)oxy]propionate

Product 1

HCID 30627972-((4-Oxo-3-phenyl-4H-1-benzopyran-7-yl)oxy)propanoic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20 g of 7-(1-ethoxycarbonylethyl)oxy-3-phenyl-4H-1-benzopyran-4-one, 200 ml of dioxane, 70 ml of hydrochloric acid and 150 ml of water was refluxed for 4 hours and poured into ice water. The resulting crystalline precipitate was collected by filtration and recrystallized from ethanol to give 17.1 g of 7-(1-hydroxycarbonylethyl)oxy-3-phenyl-4H-1-benzopyran-4-one as white crystals. m.p. 223° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationThe resulting crystalline precipitate was collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ce9c24a4f6ea45f18a9d5252defdb5da
Source dataset
uspto-grants-1987_02
Patent number
US04644012

Linked notes

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