Acetic Anhydride → 2-Allylhexanal

Temperature

120.5 °C

1,1-Bis(allyloxy)hexane (118.98 g, 0.60 mol) was dissolved in N,N-dimethylacetamide (320 mL) under a nitrogen atmosphere. To the solution, acetic anhydride (170 mL, 1.80 mol) and maleic acid (3.48 g, 0.03 mol) were added, and the mixture was stirred. The reaction mixture was warmed to 115 to 126° C., stirred at this temperature for 25 hours, and then cooled to 10° C. or lower. To the reaction mixture, toluene (480 mL) and water (720 mL) were added, and a 50% aqueous sodium hydroxide solution (294 mL) was slowly added with stirring to separate an organic layer. The aqueous layer was subjected to extraction with toluene (240 mL), and the extract was combined with the organic layer and then washed with 10% saline (240 mL). The organic layer was dried over sodium sulfate. After filtration, the filtrate was used in the next step without being concentrated or purified.

1. stirringstirred at this temperature for 25 hours
2. temperaturecooled to 10° C.
3. stirringwith stirring
4. customto separate an organic layer
5. extractionThe aqueous layer was subjected to extraction with toluene (240 mL)
6. washwashed with 10% saline (240 mL)
7. dry with materialThe organic layer was dried over sodium sulfate
8. filtrationAfter filtration
9. concentrationwithout being concentrated
10. custompurified

ORD record

ord-b49cb97cf1c54fa3bdb7d5addc2601af

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09162971B2