Pyridine → 6,8-dichlorooctanoic Acid

HRID 2984ノート

反応式

HRID 2984 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 99644476,8-dichlorooctanoic Acid

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

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).

後処理

  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

出典と根拠

ORDレコード
ord-a7e0a7be4dd4457c99da60d09cb113ab
出典データセット
uspto-grants-1998_03
特許番号
US05731448

反応ノート

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