Furan → HCID 21224573, compound
Reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[O:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)[CH3:2].[H][H].O1C=C[CH:16]=[CH:15]1>C(O)C.[Pt]>[CH2:15]([O:10][CH2:9][C:8]1[O:11][C:5]([CH2:4][O:3][CH2:1][CH3:2])=[CH:6][CH:7]=1)[CH3:16]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 7.5 ml batch reactor, 0.06 mmol 5-(ethoxymethyl)furfural (EMF) in 1 mL ethanol and 5 bars of hydrogen was reacted with 3 mol % of a Pt/C catalyst for 4 days at room temperature. The starting material was completely converted in 100% selectivity to 5-(ethoxymethyl)-2-hydroxymethyl)furan. Subsequently, the mixture was heated to 75° C. for 1 day without hydrogen. The 5-(ethoxymethyl)-2-hydroxymethyl)furan was fully converted and 2,5-bis(ethoxymethyl)furan was obtained in 80% yield. 20% Side products are ring opened levulinate derivatives. The experiment was successfully repeated on a 20 gram scale.
Sources & evidence
- ORD record
- ord-afb06bf215504869b70f16bbcac0c03b
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08231693B2
Reaction notes
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