Ethanol → Ethyl 8-bromooctanoate

Thionylchloride (8.15 ml, 0.112 mols) was added dropwise to an ethanol (500 ml) solution of 8-bromooctanoic acid (50.0 g, 0.224 mols) with cooling with ice, and the reaction mixture was then stirred for 12 hours at room temperature. The reaction mixture was concentrated in vacuo, and a saturated aqueous sodium bicarbonate solution was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated in vacuo. The thus-obtained crude product was purified by alumina column chromatography (hexane) to obtain the entitled compound (51.6 g) as an oil.

1. temperaturewith cooling with ice
2. concentrationThe reaction mixture was concentrated in vacuo
3. additiona saturated aqueous sodium bicarbonate solution was added to the residue, which
4. extractionwas then extracted with ethyl acetate
5. washThe organic layer was washed with water
6. dry with materiala saturated aqueous sodium chloride solution, then dried
7. concentrationconcentrated in vacuo
8. customThe thus-obtained crude product
9. customwas purified by alumina column chromatography (hexane)

ORD record

ord-795cdd2809c146ce9fd2d2c98e04a1da

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06326369B1