Hydrochloric Acid → 4'-Formyl-2,5-dihydroxy-1,1'-biphenyl

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Reaction Steps

A mixture of about 4.4 g. (0.01 mole) of 4'-dibromomethyl-2,5-diacetoxy-1,1'-biphenyl, prepared as described in Example 2, and about 4.4 g. (0.03 mole) of sodium acetate trihydrate in a mixture of 50 ml. of methanol and 25 ml. of water was heated at reflux under nitrogen for about 4 hours. 5 ml. of concentrated hydrochloric acid were added and refluxing continued for an additional 11/2 hours. Most of the methanol was removed by evaporation on a steam bath under nitrogen resulting in precipitation of a light cream colored solid. The mixture was diluted with 50 ml. of water, cooled in an ice bath, and the resultant solid filtered, washed with water, and dried in a vacuum oven. Yield of about 2.0 g. of 4'-formyl-2,5-dihydroxy-1,1'-biphenyl, m.p. 203°-205° C. Thin layer chromatography indicated one component. Proton nuclear magnetic resonance and infrared spectra confirmed the structure and were essentially identical to the spectra obtained from the product of Example 3. The product gave a positive test with 2,4-dinitrophenylhydrazine spray reagent.

Provenance & Evidence