4-Ethyl-2-hexenoate → 4-Ethylhexanoic acid

Eethyl 4-ethyl-2-hexenoate (55.3 g) was dissolved in a mixture of tetrahydrofuran (150 mL) and ethanol (150 mL). To the solution was added 5 w/w % palladium on activated carbon (5.5 g). The mixture was stirred at RT for 3.5 hr under hydrogen atmosphere (1 atm). The 5 w/w % palladium on activated carbon was filtered off using Celite. To the filtrate was added aqueous 4 N sodium hydroxide (111 mL). The mixture was stirred at RT overnight. The reaction mixture was washed with hexane. To the aqueous layer was added 4 N hydrochloric acid (113 mL). The mixture was extracted with ethyl acetate. The organic layer was washed with water/brine=1/1 (300 mL) and brine (150 mL), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (47.0 g) as a crude product.

1. filtrationwas filtered off
2. additionTo the filtrate was added aqueous 4 N sodium hydroxide (111 mL)
3. stirringThe mixture was stirred at RT overnight
4. washThe reaction mixture was washed with hexane
5. additionTo the aqueous layer was added 4 N hydrochloric acid (113 mL)
6. extractionThe mixture was extracted with ethyl acetate
7. washThe organic layer was washed with water/brine=1/1 (300 mL) and brine (150 mL)
8. dry with materialdried over sodium sulfate
9. filtrationThe sodium sulfate was filtered off
10. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-b755cc001884483baa59e0d96c8a159a

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604069B2