Hydrochloric Acid → 1-(4,4-Dimethyl-1-cyclopenten-1-yl)-1-ethanol

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Reaction Steps

The starting 1-(3,3-dimethyl-1-cyclopentyl)-1-ethanone was prepared thus: 2.1 g (0.088 mol) of Mg, to which a few ml of ether had been added so as to cover it, were charged into a 250 ml vessel kept under nitrogen and around ten drops of CH3I were added thereto to trigger the reaction. Once the latter had started, what was left of 11.9 g of CH3I (0.084 mol) in 30 ml of ethyl ether was introduced while maintaining a slight reflux. The mixture was then heated to reflux for 1/2 h, cooled to room temperature and 10 g (0.08 mol) of 4,4-dimethyl-1-cyclopentene-1-carbaldehyde [prepared according to Magnusson et al., J. Org. Chem. 38, 1380 (1973)], in solution in 30 ml of ether, were added thereto. It was then re-heated to reflux for 1 h. After cooling, it was poured on ice and HCl, washed to neutrality with saturated NaCl, dried, filtered and concentrated under reduced pressure. After bulb-to-bulb distillation, 6 g (yield: 53.6%) of 1-(4,4-dimethyl-1-cyclopenten-1-yl)-1-ethanol were obtained, whose analytical data were the following:

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