Allyl bromide → 1-(5-Acetyl-3-allyl-2,4-dihydroxyphenyl)ethan-1-one

HRID 435202

Reaktionsgleichung

Reaktionsgleichung von HRID 435202
[C:1]([C:4]1[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[C:7]([OH:8])=[CH:6][C:5]=1[OH:14])(=[O:3])[CH3:2].[OH-].[Na+].[CH2:17](Br)[CH:18]=[CH2:19]>O.ClCCCl>[CH2:19]([C:6]1[C:7]([OH:8])=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=[C:4]([C:1](=[O:3])[CH3:2])[C:5]=1[OH:14])[CH:18]=[CH2:17]

Komponenten

6

Edukt 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 750974,6-Diacetylresorcinol

Produkt 1

HCID 27751581-(5-Acetyl-3-allyl-2,4-dihydroxyphenyl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4,6-Diacetylresorcinol (19.4 g; 0.1 mole), sodium hydroxide (8.0 g; 0.2 mole) and allyl bromide (12.1 g; 9 ml; 0.1 mole) in water (160 ml) and 1,2-dichloroethane (150 ml) were stirred at reflux for 3 hours. The mixture was cooled to room temperature, the organic layer was separated and the aqueous layer was extracted with 1,2-dichloroethane (3×50 ml). The combined organic layers were dried (anhydrous sodium sulphate) and evaporated to give 2-allyl-4,6-diacetylresorcinol as a pink oil (9 g; 38%) which rapidly crystallised, m.p. 84°-86° C.

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with 1,2-dichloroethane (3×50 ml)
  4. dry with materialThe combined organic layers were dried (anhydrous sodium sulphate)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-16217186e512427b9a35744097503449
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04400542

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