반응 #683834

반응 방정식

5-chloro-2-thiophenecarboxylic acid

1-tetradecanol

sodium hydride

xylene

→

5-(tetradecyloxy)-2-thiophenecarboxylic acid

용매

acetic acid

반응 조건

후처리

1. 1
   온도is heated
2. 2
   온도to reflux
3. 3
   workup.ADDITIONis added
4. 4
   온도The mixture is refluxed for 64 hours after which the mixture
5. 5
   온도is cooled
6. 6
   추출extracted with the addition of ether
7. 7
   기타The ether is evaporated
8. 8
   추출aqueous layer extracted 5 times with water
9. 9
   추출The combined aqueous extract
10. 10
    기타The solid obtained
11. 11
    기타is crystallized twice from hexane

실험 절차

A mixture of 21.4 g (0.100 mole) of 1-tetradecanol, 5.9 g (0.146 mole) of sodium hydride (59.5% in oil) and 300 ml of dried xylene is heated to reflux with stirring for 2 hours then allowed to cool after which 7.5 g (0.046 mole) of 5-chloro-2-thiophenecarboxylic acid is added. The mixture is refluxed for 64 hours after which the mixture is cooled and poured into a water-ice mixture, acidified with acetic acid, and extracted with the addition of ether. The ether is evaporated and aqueous layer extracted 5 times with water: strong ammonia solution (1:1). The combined aqueous extract is acidified with acetic acid. The solid obtained is crystallized twice from hexane to give 5-(tetradecyloxy)-2-thiophenecarboxylic acid, M.P. 95°-96° C.

출처