Allyl bromide → 5-Methyl-7-(2-propen-1-yloxy)-2H-1-benzopyran-2-one

HRID 1106266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1106266
[CH3:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[O:7]2.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>>[CH3:1][C:2]1[CH:11]=[C:10]([O:12][CH2:22][CH:21]=[CH2:20])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[O:7]2

Komponenten

4

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium Carbonate2×HCID 53556397-hydroxy-5-methylcoumarin

Produkt 1

HCID 129004425-Methyl-7-(2-propen-1-yloxy)-2H-1-benzopyran-2-one

Versuchsvorschrift

A Me2CO (250 ml) solution of 5-methyl-7-hydroxycoumarin (I; 15.0 g) was reacted with allyl bromide (20 ml) in the presence of K2CO3 (5.0 g) by refluxing the mixture for 5 hours. After chilling the K2CO3 is filtered off and washed with fresh Me2CO. The pooled filtrate and acetonic washings were concentrated to dryness and the residue crystallized from cyclohexane giving 5-methyl-7-allyloxycoumarin (IV; 13.8 g; m.p. 83° ). ##STR7##

Aufarbeitung

  1. temperatureby refluxing the mixture for 5 hours
  2. filtrationis filtered off
  3. washwashed with fresh Me2CO
  4. concentrationThe pooled filtrate and acetonic washings were concentrated to dryness
  5. customthe residue crystallized from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-2c2741665dd24a78b389915e527ee9d4
Quelldatensatz
uspto-grants-1982_01
Patentnummer
US04312883

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