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Oxidation of alcohols

7 real reactions from the literature, on secondary alcohols, primary alcohols and allylic alcohols. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Alcohol oxidation: menthol (a secondary alcohol) with Na2Cr2O7; aq. H2SO4 gives p-menthan-3-one (the six-membered cyclic ketone).

  2. Alcohol oxidation: a primary alcohol with DCC, DMSO, pyridine·TFA; benzene (Pfitzner–Moffatt) gives the aliphatic aldehyde.

  3. Alcohol oxidation: cyclooctanol (a secondary alcohol) with CrO3, H2SO4; H2O, acetone gives cyclooctanone (the eight-membered cyclic ketone).

  4. Alcohol oxidation: 4-cyclopentene-1,3-diol (an allylic alcohol) with CrO3, H2SO4; aq. CH2Cl2, 0 °C gives 2-cyclopentene-1,4-dione (the α,β-unsaturated ketone).

  5. Alcohol oxidation: a secondary alcohol with Na2Cr2O7; H2SO4, AcOH; H2O, benzene gives the six-membered cyclic ketone.

  6. Alcohol oxidation: a secondary alcohol with (tBuO)3Al; acetone, benzene, Δ gives the α,β-unsaturated ketone.

  7. Alcohol oxidation: 1-butanol (a primary alcohol) with Na2Cr2O7; (2 equiv.); 3; H2SO4; (6 equiv.); (8 equiv.); H2O gives butyl butyrate (the ester).