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Clemmensen reduction

4 real reactions from the literature, on aryl ketones, six-membered cyclic ketones and aromatic aldehydes. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Clemmensen: 1-(2-hydroxyphenyl)hexan-1-one (an aryl ketone) with mossy Zn(Hg); aq. HCl, CH3CH2OH, Δ gives 2-hexylphenol (the deoxygenated product).

  2. Clemmensen: 3-benzoylpropionic acid (an aryl ketone) with Zn(Hg); HCl, H2O; toluene, Δ gives 4-phenylbutyric acid (the deoxygenated product).

  3. Clemmensen: a six-membered cyclic ketone with Zn, HCl; ether, −20-0 ¬∫C gives the deoxygenated product.

  4. Clemmensen: 3-hydroxy-2-methoxybenzaldehyde (an aromatic aldehyde) with Zn(Hg); HCl, Δ gives 2-methoxy-3-methylphenol (the deoxygenated product).