4-Hydroxybenzoic Acid → Tetradecyl 4-hydroxybenzoate

HRID 654212

Reaktionsgleichung

Reaktionsgleichung von HRID 654212
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:13](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][CH3:26]>O>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1354-Hydroxybenzoic AcidHCID 8208Myristyl bromideHCID 14798Sodium Hydroxide

Produkt 1

HCID 328882Tetradecyl 4-hydroxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 2.76 g (20 mmol) of 4-hydroxybenzoic acid and 800 mg (200 mmol) of sodium hydroxide in 12 ml of water was added 250 mg of methyl tricaprylammonium chloride and 4.67 g (17 mmol) of n-tetradecylbromide. The mixture was heated at reflux for 4 h and then diluted with 30 ml of water. The mixture was extracted with 2×30 ml ether. The ether extracts were combined and washed with water and saturated NaCl solution. The solvent was removed in-vacuo and the residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a white solid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. extractionThe mixture was extracted with 2×30 ml ether
  4. washwashed with water and saturated NaCl solution
  5. customThe solvent was removed in-vacuo
  6. customthe residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e1debb43b1474c04b16f6393d87f1724
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05130335

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