Hydrochloric Acid → 2-(2-Nitro-4-chlorophenoxy)benzyl alcohol

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Reaction Steps

10 Parts 2-(2-nitro-4-chlorophenoxy)benzaldehyde and 2.4 parts sodium cyanoborohydride is dissolved with stirring in a mixture of 22 parts of tetrahydrofuran, 20 parts methanol and 10 parts by volume 2,2,2-trifluoroethanol. To the resulting mixture is added a trace of methyl orange and a sufficient amount of 2 N hydrochloric acid in methanol to attain a deep red color. Stirring is continued for approximately 24 hours at which time the solvents are removed in vacuo. The red, oily residue is dissolved in water and ethyl ether, and the ether layer separated. The water layer is extracted three times with 18 parts portions of ethyl ether. The ether extracts are combined with the ether layer, and extracted once with 50 parts of water. The ether is removed in vacuo to give crude 2-(2-nitro-4-chlorophenoxy)benzyl alcohol which is purified by chromatography.

Provenance & Evidence