Myristyl bromide → 3,4-Bis(tetradecyloxy)benzoic acid methyl ester

HRID 248009

Reaktionsgleichung

Reaktionsgleichung von HRID 248009
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([OH:11])[CH:5]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CC(=O)CC>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:6]([O:11][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[CH:5]=1

Komponenten

6

Edukt 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 287064Methyl 3,4-Dihydroxybenzoate

Produkt 1

HCID 120485573,4-Bis(tetradecyloxy)benzoic acid methyl esterAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 15.0 g of product from Example 102, 53.2 g of 1-bromotetradecane, 37 g of potassium carbonate, 1.04 g of potassium iodide and 350 ml of 2-butanone is heated at reflux for 28.5 hours. The reaction is cooled to room temperature, filtered and the filtrate concentrated in vacuo. The residue is recrystallized from methylene chloride/hexane to give 49.33 g of the desired product.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 28.5 hours
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue is recrystallized from methylene chloride/hexane

Quellen und Nachweise

ORD-Eintrag
ord-1c278a233c4c4e89bb4e6d6464fbe472
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208247

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