Реакция #304727

Уравнение реакции

1-octadecanol

chloroacetic acid

sulfuric acid

→

Octadecyl 2-chloroacetate

Растворители

toluene

diethyl ether

Условия реакции

Обработка

1. 1
   Другоеequipped with a Dean-Stark trap
2. 2
   Экстракцияextracted twice with a saturated bicarbonate solution (500 mL)
3. 3
   ЭкстракцияThe aqueous phase was subsequently extracted with 400 mL of diethyl ether
4. 4
   СушкаThe combined organic layers were dried with sodium sulfate
5. 5
   Другоеevaporated in vacuo
6. 6
   Другоеyielding a brown solid, which
7. 7
   Другоеwas used without further purification

Методика

A solution of 1-octadecanol 5 (5 0 g, 180 mmol), chloroacetic acid (17.5 g, 180 mmol) and concentrated sulfuric acid (0.1 mL) in 350 mL of toluene was refluxed overnight in a flask equipped with a Dean-Stark trap. The solution was diluted with 500 mL of diethyl ether and extracted twice with a saturated bicarbonate solution (500 mL). The aqueous phase was subsequently extracted with 400 mL of diethyl ether. The combined organic layers were dried with sodium sulfate and evaporated in vacuo yielding a brown solid, which was used without further purification. 1H-NMR (CDCl3) δ=4.20 (t, 2H), 4.07 (s, 2H), 1.68 (q, 2H), 1.30 (m, 30H), 0.89 (t, 3H) ppm. FT-IR: ν=2919, 2851, 1749 (C═O stretch), 1333, 1208 (C—O stretch), 786 cm−1.

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