Hydrochloric Acid → HCID 13536822, compound

HRID 236344Notes

Reaction equation

HRID 236344 reaction equation
C([O:3][C:4]([CH:6]([O:8][C:9]1[CH:26]=[CH:25][C:12]2[C:13](=[O:24])[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[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:26]=[CH:25][C:12]2[C:13](=[O:24])[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=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 13558650HCID 13558650, compound

Product 1

HCID 13536822HCID 13536822, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0 g of 7-(1-ethoxycarbonylethyl)oxy-3-(3-hydroxyphenyl)-4H-1-benzopyran-4-one, 90 ml of dioxane, 120 ml of water and 15 ml of hydrochloric acid was refluxed for 2.5 hours, poured into ice water and extracted with ethyl acetate. The extract was washed with water and concentrated and the residue was recrystallized from ethyl acetate-dichloroethane to give 2.5 g of 7-(1-hydroxycarbonylethyl)oxy-3-(3- hydroxyphenyl)-4H-1-benzopyran-4-one as white crystals. m.p. 218°-219° C.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. concentrationconcentrated
  5. customthe residue was recrystallized from ethyl acetate-dichloroethane

Sources & evidence

ORD record
ord-7de4048026d34346bf225545cba7aa57
Source dataset
uspto-grants-1987_02
Patent number
US04644012

Reaction notes

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