Reacción #2460305

Ecuación de reacción

2-(1-naphthy)ethanol

triethylamine

dichloromethane

methacryloyl chloride

→

2-(1-naphthyl)ethyl methacrylate

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaat refluxed for 4 h
3. 3
   TemperaturaThe reaction mixture was cooled to ambient and
4. 4
   FiltraciónThe solution was filtered
5. 5
   Lavadothe filtrate was washed twice with water, once with NaHCO3
6. 6
   SecadoThe solution was dried (Na2SO4)
7. 7
   Concentraciónconcentrated
8. 8
   workup.DISTILLATIONThe product was purified by distillation at reduced pressure
9. 9
   Otrocollecting the fraction bp 120-125° C./0.08 mm
10. 10
    Otroto provide a colorless oil, mass

Procedimiento

A solution of 2-(1-naphthy)ethanol (30.0 g, 174 mmol), triethylamine (24.2 g, 239 mmol), 4-(dimethylamino)pyridine (1.1 g, 9.1 mmol), and dichloromethane (500 mL) was treated dropwise under nitrogen with methacryloyl chloride (18.9 g, 181 mmol), and then heated at refluxed for 4 h. The reaction mixture was cooled to ambient and diluted with diethyl ether. The solution was filtered and the filtrate was washed twice with water, once with NaHCO3, and once with brine. The solution was dried (Na2SO4) and concentrated to deposit a yellow oil. The product was purified by distillation at reduced pressure, collecting the fraction bp 120-125° C./0.08 mm to provide a colorless oil, mass: 36.0 g (86% theory). 1H (CDCl3): δ 2.00 (s, 3H), 3.50 (t, 2H), 4.55 (t, 2H), 5.60 (s, 1H), 6.15 (s, 1H), 7.50 (m, 4H), 7.8 (d, 1H), 7.9 (d, 1H), 8.2 (d, 1H).

Fuente