Pyridine → 6,8-dichlorooctanoic Acid

HRID 2983Notes

Reaction equation

HRID 2983 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4](O)[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].N1C=CC=CC=1.S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][CH:4]([CH2:3][CH2:2][Cl:1])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 109544588-Chloro-6-hydroxyoctanoic acid

Product 1

HCID 99644476,8-dichlorooctanoic Acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 2.4 g (11.0 mmoles) of the methyl ester of (+)-8-chloro-6hydroxy-octanoic acid (+)-(VIII) (R=Me) and 0.04 g (0.5 mmoles) of pyridine in 8 ml toluene, 1.6 g (13.5 mmoles) of thionyl chloride in 5 ml of toluene were added slowly. The mixture was then refluxed for 1 hour. After cooling to room temperature, the reaction mixture was added to 20 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 2.0 g (81% of the theoretical yield). [α]D20 =-30.0° (c=1, benzene).

Workup

  1. temperatureThe mixture was then refluxed for 1 hour
  2. customthe organic phase was separated
  3. washwashed with 10 mL of water
  4. dry with materialdried over magnesium sulfate
  5. customAfter that, the solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-ad0e6003b3be4ab6ac0a6c1f57d6ff26
Source dataset
uspto-grants-1998_03
Patent number
US05731448

Reaction notes

Loading…