Reacción #67776

Ecuación de reacción

acrylic acid

triethylamine

Acryloyl chloride

→

acrylic anhydride

Rendimiento 80.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe NH4+Cl− precipitate was collected in a fritted glass
2. 2
   Filtraciónfilter
3. 3
   Otrothe solvent was then removed from the filtrate by rotary evaporation
4. 4
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (25 mL)
5. 5
   Lavadowashed twice with dilute aq. NaHCO3 (50 mL each)
6. 6
   Otro(50 mL), and dried over anhy
7. 7
   FiltraciónAfter filtration
8. 8
   Otroremoving the solvent
9. 9
   Otroby rotary evaporation

Procedimiento

Acrylic anhydride was synthesized in 70-80% yield as in the following example. Acryloyl chloride (2.7 g, 30 mmol) was added dropwise over 5 min to an ice-cooled solution of acrylic acid (2.0 g, 30 mmol) and triethylamine (2.8 g, 30 mmol) in THF (50 mL), and the solution was stirred at room temperature for 16 h. The NH4+Cl− precipitate was collected in a fritted glass filter, and the solvent was then removed from the filtrate by rotary evaporation. The residue was dissolved in CH2Cl2 (25 mL), washed twice with dilute aq. NaHCO3 (50 mL each) and once with satd. NaCl aq. soln. (50 mL), and dried over anhy. Na2SO4. After filtration and removing the solvent by rotary evaporation, 2.8 g (80%) of acrylic anhydride was obtained as a light yellow liquid. It was used without further purification. 1H NMR (CDCl3, 77.23 ppm): 6.04 (m, ═CH trans to CO2), 6.14 (m, ═CH gem to CO2), 6.50 (d, ═CH cis to CO2). 13C NMR (CDCl3/DMSO-d6): 127.4 (═CH), 134.7 (′CH2), 161.2 (C═O).

Fuente