6,8-dichlorooctanoic acid synthesis

Yield:41443-60-1 80%

Reaction Conditions:

with pyridine;sodium hydroxide;thionyl chloride in (2S)-N-methyl-1-phenylpropan-2-amine hydrate;toluene

Steps:

11 EXAMPLE 11
EXAMPLE 11 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).

References:

Arzneimittelwerk Dresden GmbH US5731448, 1998, A

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