Acetic Acid → Levoglucosenone

HRID 335545Notes

Reaction equation

HRID 335545 reaction equation
[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]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 699486Levoglucosenone

Product 2

HCID 699486LevoglucosenoneHCID 11040815HCID 11040815, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

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.

Workup

  1. customto reaction completion (2.5 hours)
  2. customproduced HMF in a 16% yield

Sources & evidence

ORD record
ord-59a1dad330264d2c864a131dc4d734c7
Source dataset
uspto-grants-2014_11
Patent number
US08884036B2

Reaction notes

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