Methanol → Methyl 2-furoate

Temperature

80 °C

With reference to the chemical reaction formula 6, 2-furan carboxylic acid (20 g, 178 mmol) and 0.5M of HCI/methanol (400 mL) are put in one after another to be dissolved in an 1 L round-bottom flask and are refluxed at 80° C. for 2 hours to be reacted. After the solvent is removed by vacuum drying, the residue from which is diluted in EtOAc to be moved to a separatory funnel, and washed in turn with ice water and 5% of sodium bicarbonate (NaHCO3) aqueous solution, with pH checked at 7˜8 at the end. After moisture in the funnel is removed by MgSO4, the residue having been filtered and vacuum evaporated is separated by flash chromatography (hexanes: EtOAc=10:1) to obtain a 2-furan carboxylic acid methyl ester (20.53 g, 162 mmol, 91% of yield), in the form of light yellow oil. The data of1H and 13C-NMR referring to that is as below.

1. dissolutionanother to be dissolved in an 1 L round-bottom flask
2. customto be reacted
3. customAfter the solvent is removed by vacuum
4. customdrying
5. additionthe residue from which is diluted in EtOAc
6. customto be moved to a separatory funnel
7. washwashed in turn with ice water and 5% of sodium bicarbonate (NaHCO3) aqueous solution, with pH
8. customAfter moisture in the funnel is removed by MgSO4
9. filtrationthe residue having been filtered
10. customvacuum evaporated
11. customis separated by flash chromatography (hexanes: EtOAc=10:1)

ORD record

ord-03f4dbf271cd47d5a151e5cc65767523

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09035018B2