Sulfuric Acid → 5-Oxo-2-tetrahydrofurancarboxylic acid

Participants

Reaction Steps

In 200 ml. of water is suspended 29.4 g. (0.2 M) of H.Glu.OH, and a solution of 16.8 g. (0.24 M) of sodium nitrite in 120 ml. of water and 120 ml. of 2N-H2SO4 are simultaneously added dropwise at room temperature over a period of about 90 minutes. The reaction mixture is allowed to stand for 12 hours. The water is distilled off under reduced pressure and hot acetone is added to the residue. The acetone is distilled off from the extract and the oily residue is purified by distillation under reduced pressure. The desired compound is obtained as a distillate between 170.0 and 175.0° C/O 5 mmHg. Yield 14.3 g. (55.0%); melting point: 50° C; optical rotation [α]D27 -11.4° (c=0.77, in 2N-NaOH).

Provenance & Evidence