反応 #74903

反応方程式

dinitrogen tetraoxide

2-bromo-5,6-methylenedioxy-3-phenylbenzofuran

acetic acid

acetic acid

cyclohexene-4-carboxylic acid

→

5,6-methylenedioxy-2-nitro-3-phenylbenzofuran

溶媒

water

反応条件

後処理

1. 1
   その他the yellow product is collected
2. 2
   洗浄washed with water
3. 3
   workup.DISSOLUTIONThe product is dissolved in dichloromethane
4. 4
   洗浄the solution is washed with cold 5 percent sodium hydroxide solution, water and saturated sodium chloride solution
5. 5
   その他dried
6. 6
   濃縮The solution is concentrated to dryness
7. 7
   その他to provide a yellow residue which
8. 8
   その他is recrystallized from a benzene-hexane mixture

実験手順

To a solution of 5.2 g. (0.016 mole) of 2-bromo-5,6-methylenedioxy-3-phenylbenzofuran in 225 ml. of acetic acid is added with stirring 5.0 g. (0.024 mole) of cyclohexene-4-carboxylic acid, then 2.2 g. (0.024 mole) of dinitrogen tetraoxide in 25 ml. of acetic acid. After about one hour the mixture is poured into cold water, and the yellow product is collected and washed with water. The product is dissolved in dichloromethane, and the solution is washed with cold 5 percent sodium hydroxide solution, water and saturated sodium chloride solution, then dried. The solution is concentrated to dryness to provide a yellow residue which is recrystallized from a benzene-hexane mixture, then from an isopropanol-benzene mixture to provide yellow needles of 5,6-methylenedioxy-2-nitro-3-phenylbenzofuran, m.p. 180°-183° C.

出典