1,4-Diacetylbenzene → HCID 22763540, compound

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Reaction Steps

A bishydrazone was used in Ex. 26. It may be prepared by refluxing (48 hr) 1,4-diacetylbenzene with excess hydrazine hydrate in 2B alcohol, then cooling the reaction mixture to yield the product, m.p. = 184° C (dec.). The dialdehyde used in Ex. 35 is prepared by first reducing the dimethyl ester of 1,2-bis(4-carboxyphenoxy)ethane with lithium aluminum hydride in tetrahydrofuran to form 1,2-bis(4-hydroxymethylphenoxy)ethane; m.p. = 174°-176° C. The latter is oxidized to the desired dialdehyde with ceric ammonium nitrate in glacial acetic acid/water following the general procedure described in J. Org. Chem. 32, 3865-8 (1967); m.p. = 112.5°-114° C.

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