Chloride → HCID 25190241, compound

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Reaction Steps

In a single-neck flask equipped with reflux condenser, under stirring and argon flux, the 12-ethoxy-12-oxododecanoic acid (13; 1.5 g, 5.8 mmol) is solved in chloroform (20 mL). Thionyle chloride is dropped (SOCl2; 0.64 mL, 8.8 mmol) and the reaction is carried on under reflux for 3 h. The mixture is cooled down to room temperature and the solvent is eliminated under high vacuum. The obtained product is solved in dichloromethane (20 mL) and is added, at room temperature and under stirring, with a solution of hydroxylamine hydrochloride (0.61 g, 8.8 mmol) in pyridine (10 mL) leaving to react for 12 h under the same conditions. All the solvent are eliminated under high vacuum and the remaining product is solubilised in ethyl acetate (50 mL), washed with distilled water (3×20 mL). The organic phase is anhydrified with anhydrous sodium sulphate and filtered under vacuum. The solvent is evaporated and dried under high vacuum to give 1.3 g (Yield=82%) of product as a pale yellow solid.

Provenance & Evidence