Acetophenone → 1,3-Octanedione, 4-ethyl-1-phenyl-

Participants

Reaction Steps

The conditions of Example 1 were repeated except that the following amounts were used: 60% sodium hydride in mineral oil (200 g, 5.03 mol. 2.0 mol/mol acetophenone), methyl 2-ethylhexanoate (618 g, 3.91 mol, 1.5 mol/mol acetophenone), xylene (449 g), and then a solution of acetophenone (304 g, 2.53 mol) in xylene (180 g) was added over 1 h. The mixture was kept at reflux for an additional 30 min. Workup of the reaction mixture gave material having product in a crude yield of 89%. Vacuum distillation (200 mtorr) through a 15 cm Vigreux column yielded the product in the heart cut: 4-ethyl-1-phenyl-1,3-octadione (523 g, 97% pure, 2.06 mol; 81% yield; bp: 128-169° C.). Dypnone was undetectable in the product.

Provenance & Evidence