Reaktion #569315

Reaktionsgleichung

water

catechol

bromododecane

potassium carbonate

→

2-dodecyloxyphenol

Ausbeute 41.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with diethyl ether (3×100 ml)
2. 2
   WaschenThe combined ether extracts were washed with saturated sodium chloride solution (2×100 ml)
3. 3
   Trocknendried with anhydrous magnesium sulphate
4. 4
   SonstigeThe ether was removed
5. 5
   Sonstigeto give a solid
6. 6
   workup.DISTILLATIONDistillation at reduced pressure

Vorschrift

A mixture of catechol (11 g, 100 mmole), bromododecane (32.4 g, 130 mmoles) and potassium carbonate (18.2 g, 130 mmole) in dry DMF (100 ml) was stirred and heated at 60° C. for 48 h. The mixture was poured into water (500 ml) and extracted with diethyl ether (3×100 ml). The combined ether extracts were washed with saturated sodium chloride solution (2×100 ml) and dried with anhydrous magnesium sulphate. The ether was removed to give a solid. Distillation at reduced pressure gave 2-dodecyloxyphenol (11.4 g, 41%), b.p. 175° C./0.5 mmHg, (Found C, 77.80; H, 10.80; C18H30O2 requires C,77.65; H, 10.86; MS (CI) m/e 296 (M+ +NH4+), δH (200 MHz, CDCl3) 0.90(t, 3H), 1.28(br s, 18H), 1.82(q, 2H), 4.04(t, 2H), 5.70(s, 1H) and 6.85(m, 4H) and Catechol bis-decyl ether (11.2 g, 25%), b.p. 225° C./0.5 mmHg, m.p. 46° C. (Lit. 46° C.)5.

Quelle