4-Hydroxybenzyl Alcohol → 6-[4-(Hydroxymethyl)phenoxy]hexyl prop-2-enoate

HRID 28315

Reaktionsgleichung

Reaktionsgleichung von HRID 28315
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]I)(=[O:13])[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:10]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)(=[O:13])[CH:11]=[CH2:12]

Komponenten

5

Edukt 3

HCID 1254-Hydroxybenzyl AlcoholHCID 11430Potassium CarbonateHCID 11289038Acrylic acid 6-iodohexyl ester

Produkt 1

HCID 234484226-[4-(Hydroxymethyl)phenoxy]hexyl prop-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture consisting of 2.48 g of 4-hydroxybenzylalcohol, 5.64 g of 6-iodohexyl acrylate, and 2.76 g of potassium carbonate in 50 ml of DMF was stirred under nitrogen atmosphere for 3 h at 60° C. After being cooled to room temperature the reaction mixture was quenched with 100 ml 3N HCl and extracted with diethylether (2×100 ml). The combined ether extracts were washed with saturated NaCl solution, dried over sodium sulphate and concentrated to dryness to give 5.3 g of nearly pure 4-(6-acryloyloxyhexyloxy)benzylalcohol as a beige heavy oil.

Aufarbeitung

  1. temperatureAfter being cooled to room temperature the reaction mixture
  2. customwas quenched with 100 ml 3N HCl
  3. extractionextracted with diethylether (2×100 ml)
  4. washThe combined ether extracts were washed with saturated NaCl solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-baca2d09bcd849169359f86b1ed8d54e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419620B2

Verknüpfte Notizen

Wird geladen…