1,3-Dibromopropane → Methyl(E)-3-(2-(3-bromopropoxy)phenyl)-2-propenoate

HRID 322024

Reaktionsgleichung

Reaktionsgleichung von HRID 322024
[OH:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[O:7].[Br:14][CH2:15][CH2:16][CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CCCCCC>[Br:14][CH2:15][CH2:16][CH2:17][O:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1/[CH:4]=[CH:5]/[C:6]([O:8][CH3:9])=[O:7]

Komponenten

6

Edukt 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 89400Methyl 3-(2-hydroxyphenyl)prop-2-enoate

Produkt 1

HCID 22008973Methyl(E)-3-(2-(3-bromopropoxy)phenyl)-2-propenoateAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-hydroxycinnamate (1.31 g; 7.33 mmol) in 50 ml acetone was added 1,3-dibromopropane (1.50 ml; 14.8 mmol) and K2CO3 (4.36 g; 13.4 mmol). The mixture was heated to reflux for 12 h, cooled to r.t, diluted with hexane (50 ml), filtered and finally concentrated to afford the title product (1.96 g; 50% pure), which was used as such in the next step.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 12 h
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationfinally concentrated

Quellen und Nachweise

ORD-Eintrag
ord-98899ee8cd9c44fca81e76a246d0e22c
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211197B1

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