Ethanol → HCID 21224573, compound
Reaction equation
[OH:1][CH2:2][C:3]1[O:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[H][H].O[CH2:13][C:14]1OC(CO)=CC=1.[CH2:21](O)[CH3:22]>[Pt]>[CH2:13]([O:8][CH2:7][C:6]1[O:9][C:3]([CH2:2][O:1][CH2:21][CH3:22])=[CH:4][CH:5]=1)[CH3:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In a 7.5 ml batch reactor, 0.06 mmol 5-(hydroxymethyl)furfural (HMF) in 1 mL ethanol and 5 bars of hydrogen was reacted with 3 mol % of a Pt/C catalyst for 2 days at room temperature. The starting material was completely converted in 100% selectivity to 2,5-di(hydroxymethyl)furan. Subsequently, the mixture was heated to 75° C. for 1 day without hydrogen. The 2,5-di(hydroxymethyl)furan was fully converted and 2,5-bis(ethoxymethyl)furan was obtained in 75% yield. 25% Side products are ring opened levulinate derivatives. The experiment was successfully repeated on a 20 gram scale.
Sources & evidence
- ORD record
- ord-127917b3d2a543319fb9bf5f31875246
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08231693B2
Reaction notes
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