Paper
Pinacol‐Pinacolone Rearrangement of 1, 2‐Di‐(p‐methoxyphenyl)‐ethane‐1, 2‐diol and Bis‐(4‐methoxyphenyl)‐acetaldehyde in Acid Media
Published Nov 1, 1972 · W. Tadros, A. Sakla, S. Awad
Helvetica Chimica Acta
7
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Abstract
1, 2-Di-(p-methoxyphenyl)-ethane-1, 2-diol gave in acid media bis-(4-methoxy-phenyl)-acetaldehyde, 4-4′-dimethoxy-deoxybenzoin, and 1, 2-di-(p-methoxyphenyl)-ethylene oxide; their respective yields being influenced by at least 3 factors: (i) the acid, (ii) its concentration, and (iii) the reaction period. Bis-(4-methoxyphenyl)-acetaldehyde rearranged to the deoxybenzoin in boiling sulfuric (50%) or phosphoric (75%) acids (w/w), and to two isomeric 1, 2-diacetoxy-1, 2-di-(p-methoxyphenyl) ethanes when it was heated with acetic anhydride. The mechanisms of these reactions are discussed.
In acid media, 1, 2-Di-(p-methoxyphenyl)-ethane-1, 2-diol can produce bis-(4-methoxy-phenyl)-acetaldehyde, 4-4′-dimethoxy-deoxybenzoin, and 1,
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