6,8-dichlorooctanoic acid synthesis
- Product Name:6,8-dichlorooctanoic acid
- CAS Number:41443-60-1
- Molecular formula:C8H14Cl2O2
- Molecular Weight:213.1
90435-60-2
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41443-60-1
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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
1070-64-0
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41443-60-1
164 suppliers
$55.00/10g