Reacción #1447076

Ecuación de reacción

HCl

6-hydroxyhexanoic acid

2,6-di-tert-butyl-4-methylphenol

Acryloyl chloride

→

6-acryloyloxyhexanoic acid

Disolventes

water

pyridine

dimethylacetamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for another 2 hrs
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe combined organic layer washed with water
4. 4
   Otrodried
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated

Procedimiento

A mixture of 6-hydroxyhexanoic acid (10 g), 2,6-di-tert-butyl-4-methylphenol (0.5 g), and dimethylacetamide (57 mL) was cooled to 0° C. Acryloyl chloride (17.2 g) was then added dropwise. After stirring for 3.5 hrs, pyridine (12 mL) and water (12 mL) were slowly added. After stirring for another 2 hrs, the solution was acidified with dilute HCl and extracted with ethyl acetate. The combined organic layer washed with water, dried, filtered, and concentrated to afford 6-acryloyloxyhexanoic acid. 1H NMR (CDCl3, 500 MHz) δ 1.46 (m, 2H), 1.70 (m, 4H), 2.37 (t, J=7.3 Hz, 2H), 4.17 (t, J=6.4 Hz, 2H), 5.82 (d, J=10.4 Hz, 1H), 6.12 (dd, J=17.3, 10.5 Hz, 1H), 6.39 (d, J=17.3 Hz, 1H), 11.59 (br, 1H).

Fuente