Réaction #1869153

Équation de réaction

HCl

ethyl 3,3-ethylenedioxydodecanoate

LiOH.H2O

THF

→

3,3-ethylenedioxydodecanoic acid

Rendement 81.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate (3×50 mL)
2. 2
   Lavagewashed once with brine
3. 3
   SéchageThe organic phase was dried (MgSO4)
4. 4
   Concentrationconcentrated

Mode opératoire

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.

Source