Reduction by Sodium – Ammonia Solutions

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REDUCTION of methoxybenzene derivatives by the sodium–ammonia–alcohol reagent followed by acid hydrolysis leads to the formation of a number of hitherto inaccessible unsaturated ketones1. The process fails with some compounds because of their insolubility in liquid ammonia, a typical example being hexæstrol dimethyl ether (I, R = CH3). This substance has been treated under a variety of conditions and with admixed solvents, for example, ether or ethylenediamine, but so far without success.

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    Birch, J. Chem. Soc., 593 (1946).

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BIRCH, A., MUKHERJI, S. Reduction by Sodium – Ammonia Solutions. Nature 163, 766 (1949) doi:10.1038/163766a0

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