Reaction #2460305

Reaction equation

2-(1-naphthy)ethanol

triethylamine

dichloromethane

methacryloyl chloride

→

2-(1-naphthyl)ethyl methacrylate

Solvents

diethyl ether

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat refluxed for 4 h
3. 3
   TemperatureThe reaction mixture was cooled to ambient and
4. 4
   FiltrationThe solution was filtered
5. 5
   Washthe filtrate was washed twice with water, once with NaHCO3
6. 6
   DryingThe solution was dried (Na2SO4)
7. 7
   Concentrationconcentrated
8. 8
   workup.DISTILLATIONThe product was purified by distillation at reduced pressure
9. 9
   Othercollecting the fraction bp 120-125° C./0.08 mm
10. 10
    Otherto provide a colorless oil, mass

Procedure

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).

Source