Allyl bromide → HCID 19065246, compound

HRID 1780018Notes

Reaction equation

HRID 1780018 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[O:20][C:19]3[CH:18]=[C:17]([OH:21])[CH:16]=[C:15]([OH:22])[C:14]=3[C:12](=[O:13])[CH:11]=2)=[CH:7][C:8]=1[OH:9].[CH2:23](Br)[CH:24]=[CH2:25]>CO.[K]>[OH:22][C:15]1[C:14]2[C:12](=[O:13])[CH:11]=[C:10]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH2:25][CH:24]=[CH2:23])[CH:7]=3)[O:20][C:19]=2[CH:18]=[C:17]([OH:21])[CH:16]=1

Participants

5

Reactant 2

HCID 7841Allyl bromideHCID 5281612Diosmetin

Product 1

HCID 19065246HCID 19065246, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 5462222PotassiumSolvent

Procedure

20 g of diosmetin are dissolved in a mixture of 400 ml of anhydrous methanol and 13.3 g of potassium pellets. The reaction mixture is maintained at room temperature and then 16 g of allyl bromide dissolved in 40 ml of methanol are added dropwise with stirring. Stirring is then continued for 48 hours, and the solvents and volatile products are subsequently distilled off under reduced pressure at room temperature. The residue is taken up in 400 ml of CH2Cl2, and the insoluble material is collected by filtration and then recrystallised from 440 ml of isopropanol to yield 19 g of the expected compound, m.p.: 219° C.

Workup

  1. additionare added dropwise
  2. stirringStirring
  3. distillationthe solvents and volatile products are subsequently distilled off under reduced pressure at room temperature
  4. filtrationthe insoluble material is collected by filtration
  5. customrecrystallised from 440 ml of isopropanol

Sources & evidence

ORD record
ord-552992bda6cf42a5a98320cb5afbf0ab
Source dataset
uspto-grants-1997_05
Patent number
US05629339

Reaction notes

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