Water → 11-Azidoundecanoic acid

Participants

Reaction Steps

Crunched sodium hydroxide (709 mg, 17.7 mmol) was added to a solution of methyl 11-azidoundecanoate (4.03 g, 17.7 mmol) in methanol (75 ml). The reaction mixture was stirred for 16 h at room temperature. Water (50 ml) was added. The mixture was acidified to pH 2 by addition of a 10% aqueous solution of sodium hydrogensulphate and was extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over sodium sulphate. The solvent was removed in vacuo. The residue was dissolved in methanol (50 ml). Crunched sodium hydroxide (1.42 g, 35.4 mmol) was added. The reaction mixture was stirred at room temperature for 16 h. Water (50 ml) was added. The mixture was acidified to pH 2 by addition of a 10% aqueous solution of sodium hydrogensulphate and was extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over sodium sulphate. The solvent was removed in vacuo to give 3.13 g of 11-azidoundecanoic acid.

Provenance & Evidence