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Birch reduction

4 real reactions from the literature, on acyl-deactivated arenes, alkylbenzenes, naphthalenes and anisoles. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Birch reduction: benzoic acid (an acyl-deactivated arene) with 1) Na, NH3, CH3CH2OH; 2) aq. HCl gives 2,5-cyclohexadiene-1-carboxylic acid (the 1,4-cyclohexadiene).

  2. Birch reduction: o-xylene (an alkylbenzene) with Na, NH3; CH3CH2OH, ether gives 1,2-dimethyl-1,4-cyclohexadiene.

  3. Birch reduction: 2-ethoxynaphthalene with Na; CH3CH2OH, Δ gives 3-ethoxy-1,2-dihydronaphthalene (the 1,4-cyclohexadiene).

  4. Birch reduction: anisole with Li, (CH3)3OH; liq. NH3, THF gives 1-methoxycyclohexa-1,4-diene (the 1,4-cyclohexadiene).