Pyridine → 6,8-dichlorooctanoic Acid

To a solution of 3.0 g (15.4 mmoles) of (-)-8-chloro-6-hydroxy-octanoic acid (-)-(VI) and 0.06 g (0.8 mmoles) of pyridine in 40 ml toluene, 4.1 g (34.4 mmoles) of thionyl chloride were added slowly. The mixture was then refluxed for 1 hour, cooled to room temperature and added to 60 ml of ice water. The organic phase was then removed, washed with 20 ml of water and stirred for 4 hours with 35 ml of 2N NaOH. The aqueous phase was then removed, adjusted to a pH of 1 with 3N HCl and extracted twice with 20 ml of diethylether. The combined ether extracts were dried over magnesium sulfate. After that, the solvent was evaporated under vacuum. (+)-6,8Dichloro-octanoic acid (+)-(VII) was obtained in a yield of 2.6 g (80% of the theoretical yield). [α]D20 =+30.5° (c=1; benzene).

1. temperatureThe mixture was then refluxed for 1 hour
2. customThe organic phase was then removed
3. washwashed with 20 ml of water
4. customThe aqueous phase was then removed
5. extractionextracted twice with 20 ml of diethylether
6. dry with materialThe combined ether extracts were dried over magnesium sulfate
7. customAfter that, the solvent was evaporated under vacuum

ORD record

ord-426a0ebf081b4289a13701855d6e1618

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05731448