Ethyl Acetate → 1,3-Indandione

Participants

Reaction Steps

To a 50% dispersion of sodium hydride in mineral oil (4.55 g) was added to a solution of diethyl naphthalene 1,2-dicarboxylate (18.5 g) in ethyl acetate (22 ml.) and the mixture refluxed for 3.5 hrs. on a steam bath. After cooling the precipitated orange solid was filtered and decarboxylated with hydrochloric acid (35 ml.) in water (350 ml) at 70° C over 7 mins. to yield benze(e) indane-1,3-dione, m.p. (benzene) 178° C (decomp.) (Found: C, 79.21; H, 4.22; C13H8O2 requires: C, 79.58; H, 4.11%).

Provenance & Evidence