Butanal → 1,1-Bis[(prop-2-en-1-yl)oxy]butane

Temperature

10 °C

Butanal (100 mL, 1.11 mol) and allyl alcohol (100 g, 1.72 mol) were dissolved in hexane (400 mL) under a nitrogen atmosphere. To the solution, magnesium sulfate (82.90 g, 0.69 mol) was added, and the mixture was stirred. This mixture was cooled to 10° C. or lower, and p-toluenesulfonic acid monohydrate (3.28 g, 0.017 mol) was added thereto. The reaction mixture was stirred at 15° C. or lower for 1 hour and warmed to room temperature (approximately 25° C.), followed by further stirring for approximately 2.5 hours. The reaction mixture was cooled again to 10° C. or lower, and potassium carbonate (2.38 g) and water (400 mL) were added thereto in this order. The mixture was stirred until insoluble matter was dissolved. The organic layer was separated and then washed with water (100 mL). The obtained organic layer was concentrated under reduced pressure, and the residue was distilled (approximately 20 mmHg, 80-85° C.) to obtain the title compound (132.83 g, yield: 91%, colorless oil substance).

1. stirringThe reaction mixture was stirred at 15° C. or lower for 1 hour
2. temperaturewarmed to room temperature (approximately 25° C.)
3. stirringby further stirring for approximately 2.5 hours
4. temperatureThe reaction mixture was cooled again to 10° C.
5. stirringThe mixture was stirred until insoluble matter
6. dissolutionwas dissolved
7. customThe organic layer was separated
8. washwashed with water (100 mL)
9. concentrationThe obtained organic layer was concentrated under reduced pressure
10. distillationthe residue was distilled (approximately 20 mmHg, 80-85° C.)

ORD record

ord-ba2e53502a4c43f3b3331c630d1997c3

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09162971B2