Acetic Acid → 11-Aminoundecanoic acid

Participants

Reaction Steps

1.0 g (3.9×10-3 mol) of 11-(methoxycarbonylamino) undecanoic acid, is dissolved in 20 mL ethanol and added to 2.0 g (5.0×10-2 mol) sodium hydroxide in 2 mL water. The mixture is refluxed for 17 hours, and the resulting gold-colored solution is cooled and neutralized with acetic acid to a pH of 7. The neutralized solution is filtered to remove any salt and the filtrate is stripped to yield crude amino acid. The crude acid is dissolved in 50 mL of water, cooled in ice and filtered to yield 0.41 g (53%). Recrystallizion from 16 mL ethanol/water (3:1) resulted in 0.26 g (34% yield) 11-aminoundecanoic acid (mp. 189°-192° C., Lit. mp. 190°-192° C).

Provenance & Evidence