D-(-)-Fructose → 5-(Hydroxymethyl)furfural

HRID 1500257Notes

Reaction equation

HRID 1500257 reaction equation
[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])O)O)=O>O1CCOCC1>[CH:7]1[CH:5]=[C:3]([CH:2]=[O:1])[O:10][C:9]=1[CH2:11][OH:12]

Participants

3

Conditions

Temperature
100 °C

Procedure

14.3 g of high-fructose maize syrup (containing 10 g of carbohydrate, wherein fructose is 9 g, 50 mmol) was put into a 250 mL round-bottom flask, and 10 g of Amberlyst 15 resin was added therein. Next, 100 mL of dioxane was put into the reactor, and stirred for 3 hours at 100° C. After the reaction, Amberlyst 15 resin was filtered and removed, and the dioxane was distilled and thus to obtain a reactant compound. Ethyl acetate (100 mL) and distilled water (100 mL) were put into the obtained reactant compound. After conducting a delamination, the ethyl acetate layer was dried with magnesium sulfate (MgSO4), and the ethyl acetate was distilled, thus obtaining 4.5 g of HMF (yield rate: 71%). As a result of an 1H-NMR analysis on the obtained 5-hydroxymethyl-2-furfural (HMF), it can seen that a high-purity 5-hydroxymethyl-2-furfural (HMF) was obtained as illustrated in FIG. 2.

Workup

  1. customwas put into a 250 mL round-bottom flask
  2. addition10 g of Amberlyst 15 resin was added
  3. customAfter the reaction, Amberlyst 15 resin
  4. filtrationwas filtered
  5. customremoved
  6. distillationthe dioxane was distilled
  7. customthus to obtain a reactant compound
  8. distillationEthyl acetate (100 mL) and distilled water (100 mL)
  9. dry with materialthe ethyl acetate layer was dried with magnesium sulfate (MgSO4)
  10. distillationthe ethyl acetate was distilled

Sources & evidence

ORD record
ord-9940c04748ca4e969a2445e0015e35b0
Source dataset
uspto-grants-2015_12
Patent number
US09206148B2

Reaction notes

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