1-(Furan-2-yl)but-3-en-1-ol → HCID 12877516, compound

Temperature

55 °C

Into 350 ml of a water-acetone (1:6 by volume) mixture, was dissolved 10 g of 2-(1-hydroxy-3-butenyl)-furan. To the solution heated at 55° C. under reflux, was added dropwise 6.6 g of polyphosphoric acid. After having been stirred at 55° C. for 48 hours, the reaction mixture was stripped of the acetone by distillation and the residue was extracted twice with 300 ml of ether. The extract solution was washed with an aqueous sodium hydrogencarbonate solution, then with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and freed from the solvent by distillation to obtain 9.5 g of a concentrate. On distillation of the concentrate, there were obtained 4.2 g of 2-(1-hydroxy-3-butenyl)furan (b.p. 78° C./10 mmHg) and 3.8 g (65.5% yield based on consumed starting material) of the intended 4-hydroxy-5-allyl-2-cyclopentenone (b.p. 97° C./0.7 mmHg).

1. temperatureunder reflux
2. distillationthe reaction mixture was stripped of the acetone by distillation
3. extractionthe residue was extracted twice with 300 ml of ether
4. washThe extract solution was washed with an aqueous sodium hydrogencarbonate solution
5. dry with materialwith saturated sodium chloride solution, dried over anhydrous sodium sulfate
6. distillationfreed from the solvent by distillation
7. customto obtain 9.5 g of a concentrate
8. distillationOn distillation of the concentrate

ORD record

ord-34e0dab6ced74634bb200b93878502b0

Source dataset

uspto-grants-1984_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04465862