Myristyl bromide → 3-(Tetradecyloxy)benzenemethanol

HRID 1728546

Reaktionsgleichung

Reaktionsgleichung von HRID 1728546
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5]CO.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[OH-:26].[Na+]>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.C1(C)C=CC=CC=1>[CH2:12]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][OH:26])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

6

Edukt 3

HCID 8208Myristyl bromideHCID 14798Sodium HydroxideHCID 834043-Hydroxyphenethyl alcohol

Produkt 1

HCID 100417103-(Tetradecyloxy)benzenemethanolAusbeute 652,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 66 g of 3-hydroxyphenethyl alcohol, 147.43 g of 1-bromotetradecane, 27.65 g of sodium hydroxide and 2.15 g of trioctylmethyl ammonium chloride in 400 ml of toluene was refluxed for 42 hours. The mixture was washed with water and the organic layer dried with magnesium sulfate. The solvent was removed in vacuo and the warm concentrate poured into 1 liter of hexanes. The resulting solid was washed with cold hexanes then dried giving 998.6 g of the desired compound as a white solid.

Aufarbeitung

  1. temperaturewas refluxed for 42 hours
  2. washThe mixture was washed with water
  3. dry with materialthe organic layer dried with magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. concentrationthe warm concentrate
  6. additionpoured into 1 liter of hexanes
  7. washThe resulting solid was washed with cold hexanes
  8. customthen dried

Quellen und Nachweise

ORD-Eintrag
ord-1f9b5896a10c465a869b7a9104213deb
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05328901

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