Reaction #55648

Reaction equation

cyanoacetic acid

sodium hydroxide

4-methoxyphenyl acetaldehyde

glyme

→

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

Solvents

water

water

Conditions

Workup

1. 1
   workup.ADDITIONis added
2. 2
   OtherThe glyme is evaporated in vacuo
3. 3
   workup.ADDITIONthe residue is mixed with 10% hydrochloric acid (200 ml)
4. 4
   Temperaturerefluxed for 6.0 hours
5. 5
   TemperatureAfter cooling
6. 6
   Extractionthe mixture is extracted with ethyl acetate
7. 7
   ExtractionThe ethyl acetate extract
8. 8
   Washis washed once with brine
9. 9
   Otherdried
10. 10
    Otherevaporated
11. 11
    Washfor elution

Procedure

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.

Source