تفاعل #3080

معادلة التفاعل

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

pyridine

thionyl chloride

→

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

المذيبات

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was then refluxed for 1 hour
2. 2
   أخرىthe organic phase was separated
3. 3
   غسيلwashed with 10 mL of water
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   أخرىAfter that, the solvent was evaporated under vacuum

الإجراء التجريبي

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).

المصدر