Ethanol → Ethyl 11-bromoundecanoate

HRID 1092899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1092899
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH2:15](O)[CH3:16].C(Cl)(Cl)Cl>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 6212ChloroformHCID 1781211-Bromoundecanoic acid

Produkt 1

HCID 235144Ethyl 11-bromoundecanoateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

1000 g of 90% pure 11-bromoundecanoic acid (equivalent to 3.39 mol), 304.0 g (6.60 mol) of ethanol and 20.0 g of p-toluenesulfonic acid were introduced into 400 ml of chloroform in an experimental apparatus with water trap (for entrainers with higher specific gravity than water). The mixture was heated under reflux until water no longer separated out (about 6 hours). After the solution had cooled to room temperature it was washed successively with 1 l of water, 500 ml of saturated NaHCO3 solution and 1 l of water. The solvent was removed in vacuo. Vacuum distillation (b.p. 131-133° C./1 mbar) resulted in 716.3 g (2.44 mol, 72%) of ethyl 11-bromoundecanoate.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. customno longer separated out (about 6 hours)
  3. washwas washed successively with 1 l of water, 500 ml of saturated NaHCO3 solution and 1 l of water
  4. customThe solvent was removed in vacuo
  5. distillationVacuum distillation (b.p. 131-133° C./1 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-ab3141e402444fc9b006f268b1b62cc4
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129552B2

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