Water → HCID 19835350, compound

HRID 2291732Notes

Reaction equation

HRID 2291732 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:8][C:7]2=[O:18].O.[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl.[OH-].[Na+]>C(O)(C)C>[O:24]1[CH2:23][CH:22]1[CH2:20][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][C:9]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[CH:8][C:7]2=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 536454H-1-Benzopyran-4-one, 8-hydroxy-2-phenyl- (9CI)

Product 1

HCID 19835350HCID 19835350, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

8-Hydroxyflavone (17.9 g, 75 mmol) (see Awad et al, J. Org. Chem., 25, 1333 (1960)) was suspended in a solvent consisting of 22 ml of water and 135 ml of isopropanol. Epichlorohydrin (59 ml, 75 mmol) and NaOH (3.0 g, 75 mmol) were added and the reaction mixture was heated at 70° C. for 31/2 hours. The reaction mixture was then cooled and filtered, and the solvent was removed under reduced pressure. The residue was taken up in 600 ml of CH2Cl2, washed twice with 600 ml of H2O, dried and the remaining solvent was removed by evaporation. This gave 21.9 g of light tan solid (99% yield). The product was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationfiltered
  3. customthe solvent was removed under reduced pressure
  4. washwashed twice with 600 ml of H2O
  5. customdried
  6. customthe remaining solvent was removed by evaporation

Sources & evidence

ORD record
ord-44e0ce6905f54522bdbe124451d25dc1
Source dataset
uspto-grants-1989_01
Patent number
US04797498

Reaction notes

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