반응 #55648

반응 방정식

cyanoacetic acid

sodium hydroxide

4-methoxyphenyl acetaldehyde

glyme

→

3-[(4-methoxyphenyl)methyl]glutaric acid

용매

water

water

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   기타The glyme is evaporated in vacuo
3. 3
   workup.ADDITIONthe residue is mixed with 10% hydrochloric acid (200 ml)
4. 4
   온도refluxed for 6.0 hours
5. 5
   온도After cooling
6. 6
   추출the mixture is extracted with ethyl acetate
7. 7
   추출The ethyl acetate extract
8. 8
   세척is washed once with brine
9. 9
   기타dried
10. 10
    기타evaporated
11. 11
    세척for elution

실험 절차

To a solution of cyanoacetic acid (3.57 g), in water (20 ml) is added a solution of sodium hydroxide (2.08 g) in water (20 ml). The solution is diluted with glyme (70 ml), 4-methoxyphenyl acetaldehyde (3.0 g) is added and the mixture is left at room temperature for 6.0 hours. The glyme is evaporated in vacuo, and the residue is mixed with 10% hydrochloric acid (200 ml) and refluxed for 6.0 hours. After cooling, the mixture is extracted with ethyl acetate. The ethyl acetate extract is washed once with brine, dried, evaporated and the residue subjected to chromatography on a column of silica gel using chloroform-ethyl acetate mixtures for elution to afford 2.2 g of 3-[(4-methoxyphenyl)methyl]glutaric acid. Crystallization from a benzene-ethyl acetate-hexane mixture gives a specimen having a melting point 109°-110° C.

출처