Furfural → 1-(2-Furyl)but-3-yn-1-ol

Temperature

10 °C

In the same flask as in Example 1, there were charged granular magnesium (18.2 g), dry zinc chloride (10.2 g) and dry tetrahydrofuran (110 g). Propargyl bromide (0.88 g) was added thereto at 10° C while stirring. The resultant mixture was kept in an adiabatic condition, whereupon the reaction proceeded. When the heat generation stopped, a mixture of furfural (48.0 g), propargyl bromide (73.5 g) and toluene (110 g) was dropwise added to the reaction mixture at 30° C in 3 hours while stirring under cooling. The resultant mixture was kept at room temperature for 30 minutes while stirring. After completion of the reaction, the reaction mixture was treated in the same manner as in Example 1 and distilled under reduced pressure (65°-66° C./ 0.45 mmHg) to give 2-(1-hydroxy-3-butynyl)-furan (61.3 g) in a yield of 90% (based on the starting furfural).

1. additionwas dropwise added to the reaction mixture at 30° C in 3 hours
2. stirringwhile stirring
3. temperatureunder cooling
4. stirringwhile stirring
5. customAfter completion of the reaction
6. additionthe reaction mixture was treated in the same manner as in Example 1
7. distillationdistilled under reduced pressure (65°-66° C./ 0.45 mmHg)

ORD record

ord-1e7c2507b9444dfcbbd20320b52ab375

Source dataset

uspto-grants-1990_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04958033