Pyridine → 6,8-dichlorooctanoic Acid

To a solution of 2.4 g (12.3 mmoles) of (+)-8-chloro-6-hydroxy-octanoic acid (+)-(VI) and 0.05 g (0.6 mmoles) of pyridine in 30 ml toluene, 3.3 g (27.7 mmoles) of thionyl chloride were added slowly. The mixture was then refluxed for 1 hour. The reaction mixture was cooled to room temperature and added to 50 ml ice water. The organic phase was then removed, washed with 20 ml water and stirred for 4 hours with 30 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 diethylether. The combined ether extracts were dried over magnesium sulfate. After that, the solvent was evaporated under vacuum. (-)-6,8-dichloro-octanoic acid (-)-(VII) was obtained in a yield of 2.1 g (80% of the theoretical yield). [α]D20 =-30.6° (c=1; benzene).

1. temperatureThe mixture was then refluxed for 1 hour
2. customThe organic phase was then removed
3. washwashed with 20 ml water
4. customThe aqueous phase was then removed
5. extractionextracted twice with 20 ml 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-bc41cd91f23e45a6ab06f2b380bb0c6e

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05731448