Allyl bromide → 2',4',6'-Trihydroxy3'-(2-propenyl)acetophenone

HRID 1030683

Reaktionsgleichung

Reaktionsgleichung von HRID 1030683
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[C:3]=1[C:10](=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH:21]=[CH2:22]>O1CCCC1>[OH:1][C:2]1[C:7]([CH2:22][CH:21]=[CH2:20])=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[C:3]=1[C:10](=[O:12])[CH3:11]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 680732',4',6'-Trihydroxyacetophenone

Produkt 1

HCID 143680782',4',6'-Trihydroxy3'-(2-propenyl)acetophenoneAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 15 ml of anhydrous tetrahydrofuran was dissolved 3.0 g of 2',4',6'-trihydroxyacetophenone, and 7.4 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred at room temperature for 30 minutes. Then, 2.5 g of 3-bromo-1-propene was added to the mixture and reaction was carried out at room temperature for 3 hours. After the reaction, the reaction mixture was extracted with 500 ml of diethyl ether, and the solvent was removed from the extract by distillation. The obtained residue was recrystallized from benzene to obtain 1.5 g (yield=41.5%) of 2',4',6'-trihydroxy-3'-(2-propenyl)acetophenone in the form of a colorless prism.

Aufarbeitung

  1. additionwas added to the solution
  2. waitwas carried out at room temperature for 3 hours
  3. customAfter the reaction
  4. extractionthe reaction mixture was extracted with 500 ml of diethyl ether
  5. customthe solvent was removed from the
  6. extractionextract by distillation
  7. customThe obtained residue was recrystallized from benzene

Quellen und Nachweise

ORD-Eintrag
ord-3fabc0dff25e41778d2397b75add0719
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106871

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