Iodine → Ethyl 3-hydroxy-3-methylnonanoate

To a slurry of zinc (65.0 g, 1.0 mol) in benzene (100 ml), containing a small crystal of iodine, refluxed with stirring, was added carefully 60 ml of mixture of octan-2-one (76.8 g, 0.6 mol), ethyl bromoacetate (167.0 g, 1.0 mol) and benzene (100 ml). After initiation of the reaction, the rest of the reaction mixture was added at such a rate that reflux was maintained. After complete addition of the ketone mixture the resultant reaction mixture was boiled at reflux for a further 1 hr. The mixture was then cooled and poured into ice-cold 20% sulphuric acid (400 ml), and the mixture was extracted with diethyl ether (4×200 ml). The combined extracts were washed with water (200 ml), saturated sodium hydrogen carbonate solution (2×250 ml) and saturated sodium chloride solution until neutral. The extract was then dried (Na2SO4) and filtered and the filtrate was concentrated in vacuo to give an oil. This residual oil was distilled to afford ethyl 3-methyl-3-hydroxynonanoate (70.0 g), b.pt. 88°-90° C./0.07 mm Hg.

1. temperaturerefluxed
2. customAfter initiation of the reaction
3. additionthe rest of the reaction mixture was added at such a rate
4. temperaturethat reflux
5. temperaturewas maintained
6. customreaction mixture
7. temperatureat reflux for a further 1 hr
8. temperatureThe mixture was then cooled
9. extractionthe mixture was extracted with diethyl ether (4×200 ml)
10. washThe combined extracts were washed with water (200 ml), saturated sodium hydrogen carbonate solution (2×250 ml) and saturated sodium chloride solution until neutral
11. dry with materialThe extract was then dried (Na2SO4)
12. filtrationfiltered
13. concentrationthe filtrate was concentrated in vacuo
14. customto give an oil
15. distillationThis residual oil was distilled

ORD record

ord-37a3804e2a3a458fa8bd86458400b98d

Source dataset

uspto-grants-1981_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04294972