Acetaldehyde → 3-(Furan-3-yl)prop-2-enal

Temperature

0 °C

To a solution of 2N NaOH (115 mL) was added 3-furaldehyde (4.5 mL, 52.0 mmol) dropwise. The solution was stirred until homogeneous (approximately five minutes) and then cooled to 0° C. and acetaldehyde (1.65 mL, 57.2 mmol) in 5 mL water was added. The reaction was stirred at 0° C. for 30 min and was then diluted with ether. The mixture was separated and the aqueous layer was extracted with ether (3×50 mL). The combined organic extract was washed with brine, dried over MgSO4, filtered and evaporated to yield 4.56 g of crude product. Chromatography (silica gel ,30% ether/hexanes) yielded 2.6 g (41%) of 3-(furan-3-yl)propenal.

1. stirringThe reaction was stirred at 0° C. for 30 min
2. customThe mixture was separated
3. extractionthe aqueous layer was extracted with ether (3×50 mL)
4. extractionThe combined organic extract
5. washwas washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated
9. customto yield 4.56 g of crude product

ORD record

ord-2405e1118cce40eeb5a60aa6dd0f0044

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05112848