Methane → 4-(2-Methylpropoxy)cyclohexan-1-one

16.9 g (0.1 mole) of compound (16) were dissolved in 90 ml methanol. After adding 1.8 g of palladinised charcoal (10% Pd content), the solution was hydrogenated at room temperature and normal pressure. The catalyst was then removed and the solvent was distilled off under vacuum. The 15 g of crude product which were obtained were stirred for 1 hour at room temperature with 60 ml ether and 30 ml of 4N hydrochloric acid. This was followed by neutralisation with sodium hydrogen carbonate, separation of the ether phase, and extracting twice with ether. The ethereal solution was dried over sodium sulphate and the ether was distilled off. The 10.5 g of oil obtained were purified with 1:1 diisopropyl ether/n-hexane via a silica gel column. 6.85 g of compound (21) were obtained in a yield of 40% theoretical.