Reaction #833525

Reaction equation

Acrylic acid chloride

(4-(6-hydroxyhexyloxy)phenyl)propionic acid

N,N-dimethylaniline

dioxane

→

(4-(6-acryloyloxyhexyloxy)phenyl)propionic acid

Yield 88.5%

Solvents

heptane

ethyl acetate

water

toluene

Conditions

Workup

1. 1
   WashThe ethyl acetate layer was washed with water
2. 2
   Dryingdried over anhydrous magnesium sulfate
3. 3
   OtherThe solvent was removed by distillation from the ethyl acetate layer
4. 4
   Otherto obtain solids
5. 5
   Otherre-precipitated

Procedure

Acrylic acid chloride (74.3 g) was dropped for 10 minutes to a mixture of (4-(6-hydroxyhexyloxy)phenyl)propionic acid (200 g), N,N-dimethylaniline (100 g), BHT (0.3 g), and dioxane (1,000 mL). After stirring at 60° C. for 5 hours, the reaction mixture was poured into water and stirred with addition of ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation from the ethyl acetate layer to obtain solids. The solids were dissolved in toluene and poured into plenty of heptane and re-precipitated to obtain (4-(6-acryloyloxyhexyloxy)phenyl)propionic acid (AK2: 213 g). Melting point: 64° C. to 68° C.

Source