Sulfuric Acid → HCID 10620354, compound

HRID 369424Notes

Reaction equation

HRID 369424 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=1)[O:8][C:7]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C(C)C)[CH:18]=1)=[CH:6][C:5]2=[O:27].S(=O)(=O)(O)O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=1)[O:8][C:7]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=1)=[CH:6][C:5]2=[O:27]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10646330HCID 10646330, compound

Product 1

HCID 10620354HCID 10620354, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-Bromo-8-ethoxycarbonyl-3'-isopropoxyflavone were refluxed under heat for 0.5 to 1 hour in acetic acid which contained 3% of sulfuric acid. The mixture was charged into ice water, followed by extraction with ethyl acetate. The organic layer was washed with water and 4% aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The thus-obtained crude crystals were recrystallized from ethanol, whereby the title compound was obtained (yield: 80%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and 4% aqueous solution of sodium hydrogencarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe thus-obtained crude crystals
  6. customwere recrystallized from ethanol, whereby the title compound
  7. customwas obtained (yield: 80%)

Sources & evidence

ORD record
ord-993f18e510d9417994c707fe916008d5
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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