Methanesulfonic Acid → Decyl cyanoacetate

Participants

Reaction Conditions

Reaction Steps

Cyanoacetic acid (85.5 g; 1.0 mol), decyl alcohol (206 g; 1.30 mol) and methanesulfonic acid (0.47 g; 0.005 mol) were introduced into a 500 ml flask under a nitrogen atmosphere. The mixture was warmed slowly to a maximum temperature of 130° C., while gradually reducing the pressure to about 10 mm of Hg. Water was continuously removed from the distillates (bp 60-65° C./50 mm of Hg) and the organic layer of decyl alcohol was returned to the flask until the reaction was complete. After distilling off the unreacted decyl alcohol, the decyl cyanoacetate (bp 143° C./1 mm of Hg) was isolated as a clear liquid. The yield was 219 g (97% of theoretical) with a purity of >99% (GC assay).

Provenance & Evidence