Reaction #2383778

Reaction equation

tetrahydrofuran

maleic anhydride

→

5-methylenebicyclo[2.2.1]hept-2-ene maleic anhydride

Yield 183.7%

Solvents

n-hexane

Conditions

Workup

1. 1
   Otherequipped with a thermometer, a condenser pipe, and a nitrogen inlet pipe
2. 2
   Temperaturethe mixture was heated
3. 3
   Temperatureunder reflux at 70 C
4. 4
   workup.ADDITIONwhile introducing nitrogen for 8 hr
5. 5
   Otherpolymerization
6. 6
   OtherAfter the completion of the polymerization
7. 7
   Otherto precipitate the resultant polymer, which
8. 8
   Otherwas then dried

Procedure

This synthesis example is directed to the synthesis of polymer (1b) (illustrated below as chemical formulas 14 or 15), a γ-hydroxy carboxylic acid structure. 21.2 g of 5-ethylenebicyclo[2.2.1]hept-2-ene, 19.6 g of maleic anhydride, 2.56 g of 2,2′-azobisisobutyronitrile, and 240 g of tetrahydrofuran were placed in a 500-ml, three-necked flask equipped with a thermometer, a condenser pipe, and a nitrogen inlet pipe, and the mixture was heated under reflux at 70 C. while introducing nitrogen for 8 hr to conduct polymerization. After the completion of the polymerization, the reaction mixture was poured into 1000 ml of n-hexane to precipitate the resultant polymer, which was then dried to give 37.5 g of a 5-methylenebicyclo[2.2.1]hept-2-ene/maleic anhydride copolymer (1a) (yield 92%). The polymer was analyzed by various methods and was found to mainly have a structure represented by the following formula:

Source