Reaktion #1869153

Reaktionsgleichung

HCl

ethyl 3,3-ethylenedioxydodecanoate

LiOH.H2O

THF

→

3,3-ethylenedioxydodecanoic acid

Ausbeute 81.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (3×50 mL)
2. 2
   Waschenwashed once with brine
3. 3
   TrocknenThe organic phase was dried (MgSO4)
4. 4
   Einengenconcentrated

Vorschrift

To a 25 mL flask were added ethyl 3,3-ethylenedioxydodecanoate (1.131 g, 3.95 mmol), LiOH.H2O (840 mg, 20 mmol), THF (5 mL), and water (5 mL). The mixture was stirred at room temperature overnight. The solution was acidified by the addition of 1 M HCl (50 mL), and extracted with ethyl acetate (3×50 mL). The organic layers were combined and washed once with brine. The organic phase was dried (MgSO4) and concentrated to give 3,3-ethylenedioxydodecanoic acid (0.824 g, 3.19 mmol) in 81% yield. 1H NMR (500 MHz, CDCl3) δ 0.88 (t, J=7 Hz, 3H), 1.20-1.44 (m, 14H), 1.72-1.80 (m, 2H), 2.72 (s, 2H), 3.98-4.10 (m, 4H); 13C NMR (125 MHz, CDCl3) δ 13.9, 22.5, 23.3, 29.13, 29.35, 29.39, 29.50, 31.7, 37.5, 42.2, 64.9 (2 C), 109.2, 174.8.

Quelle