1,4-Dibromobutane → 4-(4-Bromobutoxy)phenyl 4-allyloxybenzoate

HRID 1637300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637300
[CH2:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:1]([O:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([O:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:25][CH2:24][CH2:23][CH2:22][Br:21])=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 153464294-Hydroxyphenyl 4-allyloxybenzoate

Produkt 1

HCID 193489834-(4-Bromobutoxy)phenyl 4-allyloxybenzoateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

162.1 g (0.6 mol) of 4-hydroxyphenyl 4-allyloxybenzoate, known from U.S. Pat. No. 5,211,877, were dissolved in 3 l of methyl ethyl ketone, and 1.32 kg (6 mol) of commercial 1,4-dibromobutane, and 414 g (3 mol) of potassium carbonate were added. The mixture was heated to 80° C. with stirring and held at this temperature for 4 h. It was subsequently cooled, the remaining potassium carbonate was filtered off and the filtrate was concentrated. After the excess dibromobutane had been stripped off, the crude product was recrystallized twice from isopropanol. 4-(4-Bromobutoxy)phenyl 4-allyloxybenzoate was obtained in a yield of 90%. The ester shows the following phase behavior: C 64, N 81-85, isotropic.

Aufarbeitung

  1. temperatureIt was subsequently cooled
  2. filtrationthe remaining potassium carbonate was filtered off
  3. concentrationthe filtrate was concentrated
  4. customthe crude product was recrystallized twice from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-c22c61fc11c54747ab5d3c4ab6e44418
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040411

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