Acetic Acid → Levoglucosenone

Reaktionsgleichung

[CH2:1]1[O:8][C@@H:7]2[O:9][C@H:2]1[CH:3]=[CH:4][C:5]2=[O:6].C(O)(=[O:12])C>Cl>[CH2:1]1[O:8][C@@H:7]2[O:9][C@H:2]1[CH:3]=[CH:4][C:5]2=[O:6].[C@@H:7]12[O:8][CH2:1][C@@H:2]([O:9]1)[C@@H:3]([OH:12])[CH2:4][C:5]2=[O:6]

Komponenten

Versuchsvorschrift

Levoglucosenone, an isomer of HMF, can be produced from woody (lignocellulosic) material through pyrolysis. F. Shafizadeh et al. (Carbohydrate Research, 71, (1979), 169-191) found that heating levoglucosenone in 0.5 M HCl (pH=0.3) in a boiling water bath to reaction completion (2.5 hours) produced HMF in a 16% yield. Heating levoglucosenone in 2 M acetic acid (pH=2.2) produced 1,6-anhydro-3-deoxy-β-D-erythro-hexopyranos-2-ulose, (represented by Formula (I-a)) in a 77% yield, but no HMF.