D-(-)-Fructose → Isoamyl levulinate

HRID 1527827Notes

Reaction equation

HRID 1527827 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 18%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
200 °C

Procedure

In a first experiment, a mixture of crystalline fructose (10 g) in isoamyl alcohol (40 mL) and concentrated H2SO4 (0.10 mL) was placed in sealed a Teflon-lined reaction vessel inside a high-density rotor for treatment in a MicroSYNTH Microwave Labstation. The sample was heated from room temperature via microwaves to 200° C. in 3 min., and kept there for 3 min. using an irradiation power of 1000 Watts. The vessel was cooled. Analysis indicates a 59% molar yield of isoamyl HMF and 18% yield of isoamyl levulinate from fructose.

Workup

  1. customreaction vessel inside a high-density rotor for treatment in a MicroSYNTH Microwave Labstation
  2. temperatureThe vessel was cooled

Sources & evidence

ORD record
ord-9cc15420dbeb4e2fbfbb15a1f7a081c7
Source dataset
uspto-grants-2015_07
Patent number
US09090550B2

Reaction notes

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