Reacción #3080

Ecuación de reacción

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

pyridine

thionyl chloride

→

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

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was then refluxed for 1 hour
2. 2
   Otrothe organic phase was separated
3. 3
   Lavadowashed with 10 mL of water
4. 4
   Secadodried over magnesium sulfate
5. 5
   OtroAfter that, the solvent was evaporated under vacuum

Procedimiento

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).

Fuente