A novel hydroxylactone from the Lewis acid catalysed pyrolysis of cellulose

Abstract

The novel δ-lactone (1) of (3R,5S)-3-hydroxy-5-hydroxymethyltetrahydrofuran-3-carboxylic acid (2) has been isolated from tar produced by pyrolysis of cellulose doped with zinc chloride. Using Curie-point pyrolysis-g.l.c. analysis, the lactone was shown to be a significant product of the pyrolysis of cellulose in the presence of a wide variety of other Lewis acids, but not in the presence of protic acids or copper(II) chloride. The lactone (1) was readily hydrolysed to the acid (2) and yielded the methyl ester (3) on methanolysis.