4-(2-Hydroxyethyl)benzonitrile → HCID 22988443, compound

Participants

Reaction Steps

3-{4-[2-(4-Cyanophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester was synthesized using the same method as in Example 38(c) using 2-ethoxy-3-(4-hydroxyphenyl) propanoic acid ethyl ester (described in Example 20b) (6.62 g; 27.78 mmole) and p-cyanophenethyl alcohol (2.73 g; 18.52 mmole). The reaction was interrupted after 2 hours. Purification by chromatography on silica gel using first dichloromethane and then petroleum ether:diethyl ether as eluants gave a mixture of product and starting material which was dissolved in ethyl acetate and washed with sodium hydroxide (1 N). The organic phase was washed with water, dried (sodium sulfate), filtered and the solvent as evaporated to give 4.23 g (yield 62%) of 3-{4-[2-(4-cyanophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester.

Provenance & Evidence