Reaction #2460304

Reaction equation

1,3-dicyclohexyl-carbodiimide

1-napthoic acid

2-hydroxyethylmethacrylate

dimethylamino-pyridine p-toluenesulfonic acid salt

→

2-(1-naphthoyloxy)ethyl methacrylate

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was warmed to ambient and
2. 2
   FiltrationThe precipitated urea by-product was filtered
3. 3
   Washthe filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine
4. 4
   DryingThe organic layer was dried (Na2SO4)
5. 5
   Concentrationconcentrated
6. 6
   OtherThe product was purified by column chromatography
7. 7
   Otherto provide 8.2 g (62% of theory) of a pale yellow oil

Procedure

A mixture of 1-napthoic acid (8.0 g, 46 mmol), 2-hydroxyethylmethacrylate (18.1 g, 139 mmol), dimethylamino-pyridine p-toluenesulfonic acid salt (5.5 g, 19 mmol), and anhydrous dichloromethane (45 mL) was cooled to 0° C. under nitrogen, and 1,3-dicyclohexyl-carbodiimide (12.5 g, 60 mmol) were added. After 15 min, the reaction mixture was warmed to ambient and stirred for 3 h. The precipitated urea by-product was filtered, and the filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine. The organic layer was dried (Na2SO4) and concentrated to deposit a gold oil. The product was purified by column chromatography to provide 8.2 g (62% of theory) of a pale yellow oil. 1H NMR (CDCl3): δ 1.90 (s, 3H), 1.55 (m, 2H), 1.70 (m, 2H), 5.60 (s, 1H), 6.20 (s, 1H), 7.55 (m, 3H), 7.90 (d, 1H), 8.05 (d, 1H), 8.20 (d, 1H), 8.90 (d, 1H).

Source