反応 #3080

反応方程式

(-)-8-chloro-6-hydroxy-octanoic acid

pyridine

thionyl chloride

→

(+)-6,8-dichloro-octanoic acid

溶媒

toluene

toluene

反応条件

後処理

1. 1
   温度The mixture was then refluxed for 1 hour
2. 2
   その他the organic phase was separated
3. 3
   洗浄washed with 10 mL of water
4. 4
   乾燥dried over magnesium sulfate
5. 5
   その他After that, the solvent was evaporated under vacuum

実験手順

To a solution of 2.9 g (13.2 mmoles) of the methyl ester of (-)-8-chloro-6-hydroxy-octanoic acid (-)-(VIII), (R=Me) and 0.05 g (0.6 mmoles) of pyridine in 10 ml toluene, 1.9 g (16.2 mmoles) of thionyl chloride in 6 ml toluene were added slowly. The mixture was then refluxed for 1 hour. After cooling to room temperature, the reaction mixture was added to 25 ml ice water and the organic phase was separated and washed with 10 mL of water and dried over magnesium sulfate. After that, the solvent was evaporated under vacuum. The methyl ester of (+)-6,8-dichloro-octanoic acid (+)-(III), (R=Me) was obtained in a yield of 2.4 g (81% of the theoretical yield). [α]D20 =+30.1° (c=1, benzene).

出典