D-(-)-Fructose → Isoamyl levulinate

HRID 1527829Notes

Reaction equation

HRID 1527829 reaction equation
O[CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9](CO)[OH:10])O)O)=[O:4].[CH2:13]([OH:18])[CH2:14][CH:15]([CH3:17])[CH3:16]>OS(O)(=O)=O>[C:9]([O:18][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])(=[O:10])[CH2:7][CH2:5][C:3]([CH3:2])=[O:4]

Participants

4

Reactant 2

HCID 5984D-(-)-FructoseHCID 31260Isoamyl Alcohol

Product 1

HCID 522404Isoamyl levulinateYield 16%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In the third experiment, a mixture of crystalline fructose (10 g) in isoamyl alcohol (40 mL) and concentrated H2SO4 (0.10 mL) was placed in a sealed Teflon-lined reaction vessel inside a high-density rotor for treatment via microwaves in a MicroSYNTH Microwave Labstation. The sample was heated from room temperature to 160° C. in 3.5 min., and kept there for 10 min. using an irradiation power of 1000 Watts. The vessel was cooled. Analysis indicates a 55% molar yield of isoamyl HMF and 16% yield of isoamyl levulinate from fructose.

Workup

  1. customreaction vessel inside a high-density rotor for treatment via microwaves in a MicroSYNTH Microwave Labstation
  2. temperatureThe sample was heated from room temperature to 160° C. in 3.5 min.
  3. temperatureThe vessel was cooled

Sources & evidence

ORD record
ord-44ff351389154884a34ec25e5c02236a
Source dataset
uspto-grants-2015_07
Patent number
US09090550B2

Reaction notes

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