反応 #529488

反応方程式

4-t-butylazo-4-cyanovaleryl chloride

2,4-dihydroxybenzophenone

pyridine

ether

→

4-(4-t-Butylazo-4-cyanovaleryloxy)-2-hydroxybenzophenone

収率 99.0%

溶媒

water

反応条件

後処理

1. 1
   workup.ADDITIONround bottom flask containing a thermometer, condenser and magnetic stirring bar
2. 2
   workup.ADDITIONwas added 4.0 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, and 10% NaHCO3 solution and saturated sodium chloride solution
8. 8
   その他The ether was evaporated off
9. 9
   workup.DISSOLUTIONthe residue dissolved in methylene chloride
10. 10
    乾燥dried over anhydrous sodium sulfate
11. 11
    ろ過filtered

実験手順

To a solution of 4.7 g. (0.022 m) of 2,4-dihydroxybenzophenone and 2.5 ml. of pyridine in 35 ml. of ether in a 4 neck 100 ml. round bottom flask containing a thermometer, condenser and magnetic stirring bar was added 4.0 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, and 10% NaHCO3 solution and saturated sodium chloride solution. The ether was evaporated off and the residue dissolved in methylene chloride, dried over anhydrous sodium sulfate, filtered and the methylene chloride stripped off under reduced pressure. The product weighted 8.8 g. (99% yield) and was a viscous syrup. The infrared spectrum was in agreement with the structure of the desired product.

出典