Benzyl Alcohol → Isonicotinic Acid

Participants

Reaction Conditions

Reaction Steps

A sodium or potassium salt of allyl alcohol, benzyl alcohol, or substituted benzyl alcohol is dissolved in a solvent that does not affect the reaction, such as tetrahydrofuran, toluene, and dimethylformamide, and preferably dimethylformamide. A sodium salt of 2,6-dichloroisonicotinic acid is added to the resulting solution at room temperature. The resulting mixture is stirred at 60 to 100° C. for 2 to 24 hours. The mixture is allowed to react, preferably, at 80° C. for 4 hours. Here, 2 to 10 equivalent, and preferably 4 equivalent amount of alcoholate is used relative to a sodium salt of 2,6-dichloroisonicotinic acid. After the reaction has completed, water is added to the reaction product, and a water layer is separated using ethyl acetate or a like solvent. The pH of the water layer is adjusted to 5 to 6 using 1N-hydrochloric acid or acetic acid. The result is subjected to extraction using ethyl acetate, a mixed solvent of ethyl acetate and n-hexane, toluene, or the like. The extract is dried over sodium sulfate, magnesium sulfate, etc., and then concentrated to obtain an isonicotinic acid derivative of allyloxy, benzyloxy, or substituted benzyloxy (2)(in the present specification, the isonicotinic acid derivative of allyloxy, benzyloxy, or substituted benzyloxy (2) may be referred to as isonicotinic acid derivative (2)).

Provenance & Evidence