Benzene → 2,3-O-Isopropylidene-L-gulonolactone, 2,3-O-Isopropylidene-L-gulono-1,4-lactone, 2,3-O-(1-Methylethylidene)-L-gulonic Acid |A-Lactone, 94840-08-1

Participants

Reaction Conditions

Reaction Steps

2,3:5,6-Di-O-isopropylidene-L-gulonolactone (22.89 g, 88.7 mmol) was dissolved in acetic acid/water (7:1, 200 ml) and stirred at 30° C. for 16 h when t.l.c. (ethyl acetate/hexane 1:1) revealed no starting material (Rf 0.5) and one major product (Rf 0.1). The solvent was removed under reduced pressure to give a yellow oil. Trituration with benzene (50 ml) gave a solid which was shaken with ethyl acetate/acetone (1:1, 250 ml). The resulting suspension was filtered and solvents removed under reduced pressure to yield an amorphous yellow solid, which was recrystallized from ethyl acetate to yield 2,3-O-isopropylidene-L-gulonolactone, (14.31 g, 79%) as a white crystalline solid, m.p. 139°-141° C., [α]D20 +76.2° (C, 1 in acetone).

Provenance & Evidence