反応 #94172

反応方程式

4-t-butylazo-4-cyanovaleryl chloride

2,2'-dihydroxybenzophenone

pyridine

ether

→

2-(4-t-butylazo-4-cyanovaleryloxy)-2'-hydroxybenzophenone

収率 71.2%

溶媒

water

pentane

反応条件

後処理

1. 1
   その他round bottom flask equipped with a thermometer, condenser and magnetic stirring bar
2. 2
   workup.ADDITIONwas added 5.0 g
3. 3
   その他did not rise above 25° C
4. 4
   workup.ADDITIONAfter completion of the addition the reaction mixture
5. 5
   workup.ADDITIONdiluted with 100 ml
6. 6
   その他The ether layer was separated
7. 7
   洗浄washed consecutively with 5% HCl, water, 10% NaHCO3 solution and saturated sodium chloride solution
8. 8
   その他The ether was evaporated off
9. 9
   その他leaving a yellow solid
10. 10
    ろ過filtered
11. 11
    その他air dried
12. 12
    温度on heating above 80° C

実験手順

To a solution of 4.68 g. (0.0218 m) of 2,2'-dihydroxybenzophenone and 2.5 ml. of pyridine in 30 ml. of ether in a 4 neck 100 ml. round bottom flask equipped with a thermometer, condenser and magnetic stirring bar was added 5.0 g. (0.0218 m) of 4-t-butylazo-4-cyanovaleryl chloride dropwise with cooling so the temperature did not rise above 25° C. After completion of the addition the reaction mixture was stirred 1/2 hour at room temperature and then diluted with 100 ml. of water. The ether layer was separated, washed consecutively with 5% HCl, water, 10% NaHCO3 solution and saturated sodium chloride solution. The ether was evaporated off leaving a yellow solid. The solid was slurried in pentane, filtered and air dried. The product weighed 6.3 g. (71.2% yield) and decomposed slowly on heating above 80° C. The infrared spectrum of the product was in agreement with the structure of the desired product.

出典