Reaction #1121717

Reaction equation

ammonium chloride

thionyl chloride

4-{[6-(acryloyloxy)hexyl]oxy}benzoic acid

4-(6-bromohexyloxy)phenol

→

4-(6-bromo hexyloxy)phenyl 4-{[6-(acryloyloxy)hexyl]oxy}benzoate

Yield 59.9%

Solvents

tetrahydrofurane

triethyl amine

Conditions

Workup

1. 1
   Otherwas adjusted to a temperature of 0° C. (Celsius)
2. 2
   workup.STIRRINGstirred at 0° C. (Celsius) for 1 hour
3. 3
   workup.STIRRINGstirred at a room temperature overnight
4. 4
   OtherThe resulting reaction mixture
5. 5
   Extractionwas extracted three times with ethyl acetate (50 ml (milliliters)), and waster
6. 6
   Otherwas removed over magnesium sulfate
7. 7
   OtherThen, the solvents were evaporated
8. 8
   Otherthe resulting reaction mixture
9. 9
   Otherwas then purified

Procedure

4-{[6-(acryloyloxy)hexyl]oxy}benzoic acid (4) (2.8 g (grams)) was dissolved in tetrahydrofurane (THF, 100 ml (milliliters)) at a room temperature, and a temperature of the resulting mixture was adjusted to a temperature of 0° C. (Celsius). Then, thionyl chloride (12 ml (milliliters), 1M in THF) was added to the mixture, and stirred for 30 minutes. Then, 4-(6-bromohexyloxy)phenol (2.5 g (grams)) and triethyl amine (13 ml (milliliters)) were added to the resulting reaction mixture, stirred at 0° C. (Celsius) for 1 hour, and then stirred at a room temperature overnight. Next day, a saturated ammonium chloride aqueous solution was poured into the reaction mixture, and the reaction was completed. The resulting reaction mixture was extracted three times with ethyl acetate (50 ml (milliliters)), and waster was removed over magnesium sulfate. Then, the solvents were evaporated, and the resulting reaction mixture was then purified using a column chromatography (developer solution: ethylacetate/hexane=1/2 volume ratio) to obtain 4-(6-bromo hexyloxy)phenyl 4-{[6-(acryloyloxy)hexyl]oxy}benzoate (5) (3 g (grams)).

Source