Based on biogenetic considerations new syntheses of menaphthone and lawsone are given. Fromα-naphthol, 1-hydroxy-4-methoxy-2-naphthaldehyde is prepared. This undergoes Clemmensen reduction and subsequent oxidative demethylation with nitric acid to yield menaphthone. On the other hand, Dakin’s oxidation gives directly lawsone and this change involves oxidative demethylation by hydrogen peroxide in alkaline solution. A convenient laboratory method for preparing lawsone employs 2-acetyl-α-naphthohydroquinone.