Ethylene Glycol → 2-(2-Methyl[1,3]dioxolane-2-yl)furan

A mixture of 4 mL (139.6 mmol) 2-acetylfuran, 8.7 mL (156 mmol) of ethylene glycol, 198 mg (1 mmol) of p-toluenesulfonic acid monohydrate, and 22 mL (132.3 mmol) of triethyl orthoformate was reacted at room temperature under N2 for 3 days. The reaction mixture was poured into a mixture of ethyl acetate (100 mL) and water (100 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL), and the combined organic layer was washed with water (100 mL), sodium bicarbonate solution (150 mL), and brine (100 mL). The organic layer was dried over MgSO4, concentrated in vacuo, and the residue was distilled under reduced pressure (1.5 torr) to afford 9.98 g (50%) of 2-(2-methyl-1,3-dioxolan-2-yl)-furan, as a clear oil, b.p. 24° C./1.5 mm.

1. customwas reacted at room temperature under N2 for 3 days
2. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
3. washthe combined organic layer was washed with water (100 mL), sodium bicarbonate solution (150 mL), and brine (100 mL)
4. dry with materialThe organic layer was dried over MgSO4
5. concentrationconcentrated in vacuo
6. distillationthe residue was distilled under reduced pressure (1.5 torr)

ORD record

ord-b5afc5352c9a45dfb87d0deaf2e76f6e

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05665763