2,5-Furandicarboxylic acid → 2,5-Furandicarboxylic acid, tetrahydro-

HRID 1889211Notes

Reaction equation

[O:1]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=[C:2]1[C:9]([OH:11])=[O:10]>C(O)(=O)C>[O:1]1[CH:5]([C:6]([OH:8])=[O:7])[CH2:4][CH2:3][CH:2]1[C:9]([OH:11])=[O:10]

Participants

Conditions

Temperature: 140 °C

Procedure

A 100 mL pressure vessel with a glass liner and an impeller was charged with 1.87 g of furan-2,5-dicarboxylic acid, 0.5 g of 4% Pd/Silica and 40 mL of acetic acid. The pressure vessel was purged 3 times with nitrogen, and 2 times with hydrogen. The vessel was then pressurized to 750 psig hydrogen and heated to 140° C. for 3 hours. After cooling the vessel was vented and the solids were separated by filtration. The acetic acid solution was evaporated under vacuum to provide 1.68 g (88% yield) of tetrahydrofuran-2,5-dicarboxylic acid.

Workup

customThe pressure vessel was purged 3 times with nitrogen, and 2 times with hydrogen
temperatureAfter cooling the vessel
customthe solids were separated by filtration
customThe acetic acid solution was evaporated under vacuum

Sources & evidence

ORD record: ord-2ef3cade6abc469697a8e598d34d196e
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501989B2

Reaction notes

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