反応 #55648

反応方程式

cyanoacetic acid

sodium hydroxide

4-methoxyphenyl acetaldehyde

glyme

→

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

溶媒

water

water

反応条件

後処理

1. 1
   workup.ADDITIONis added
2. 2
   その他The glyme is evaporated in vacuo
3. 3
   workup.ADDITIONthe residue is mixed with 10% hydrochloric acid (200 ml)
4. 4
   温度refluxed for 6.0 hours
5. 5
   温度After cooling
6. 6
   抽出the mixture is extracted with ethyl acetate
7. 7
   抽出The ethyl acetate extract
8. 8
   洗浄is washed once with brine
9. 9
   その他dried
10. 10
    その他evaporated
11. 11
    洗浄for elution

実験手順

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.

出典