Hydrochloric Acid → beta-Cyclocitral

Participants

Reaction Steps

54.2 Ml (0.077M) of a 1.42N solution of butyl-lithium in hexane were added at -10/+15° to a solution of 10.0 g (0.055M) of methyl beta-cyclogeranate in 150 ml of anhydrous THF. After having been left at 15° during 5 mn, there were added to the reaction mixture 15.9 ml of a 70% solution of VITRIDE in toluene (0.055M). The temperature of the mixture was then raised to 40° and, at this temperature, it was left under stirring for 45 mn. The mixture was then rapidly poured at 15° onto a solution of 20.35 g (0.275M) of 2-butanol in 100 ml of THF. At the end of the reaction, 150 ml of a 5% aqueous HCl were rapidly added and an extraction was then carried out with ether. The combined organic extracts were washed, dried over Na2SO4 and concentrated to give a residue which, on distillation in a bulb apparatus, gave 7.74 g of beta-cyclocitral (purity: 76%; yield: 70%). By carrying out the hydrolysis with a saturated aqueous solution of ammonium chloride or with aqueous HCl instead of 2-butanol, a mixture of beta-/gamma-cyclocitral was obtained the isomeric content of which was of about 70/30.

Provenance & Evidence