Hydrochloric Acid → (+-)-3-Hydroxydodecanoic acid

To an ice-cooled solution of methyl 3-oxododecanoate in methanol was added sodium borohydride (83 mg). After stirring for 20 minutes, 1N-hydrochloric acid (2.2 ml) was added. After concentration, the residue was dissolved in ethyl acetate (30 ml) and 0.1 N-hydrochloric acid (20 ml). The organic phase was washed with water (20 ml), saturated aqueous sodium bicarbonate (20 ml), and brine (20 ml), dried, and concentrated. The residue was dissolved in methanol (3 ml), and to this solution was added 1N-sodium hydroxide (2.4 ml). The mixture was refluxed for an hour, and diluted with water (30 ml). This aqueous solution was washed with dichloromethane (20 ml), acidified with 1N-hydrochloric acid (2.6 ml), and extracted with ethyl acetate (30 ml). This organic phase was washed with brine (20 ml), dried, and concentrated. The residue was recrystallized from a mixture of ethyl acetate (1 ml) and n-hexane (3 ml) to give 3-hydroxydodecanoic acid (0.27 g).

1. concentrationAfter concentration
2. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
3. washThe organic phase was washed with water (20 ml), saturated aqueous sodium bicarbonate (20 ml), and brine (20 ml)
4. customdried
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in methanol (3 ml)
7. additionto this solution was added 1N-sodium hydroxide (2.4 ml)
8. temperatureThe mixture was refluxed for an hour
9. additiondiluted with water (30 ml)
10. washThis aqueous solution was washed with dichloromethane (20 ml)
11. extractionextracted with ethyl acetate (30 ml)
12. washThis organic phase was washed with brine (20 ml)
13. customdried
14. concentrationconcentrated
15. customThe residue was recrystallized from a mixture of ethyl acetate (1 ml) and n-hexane (3 ml)

ORD-Eintrag

ord-a928b2465cfe4b41b618869fc47acd66

Quelldatensatz

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06110933