Pyridine → 6,8-dichlorooctanoic Acid

HRID 2984노트

반응식

HRID 2984 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 99644476,8-dichlorooctanoic Acid

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a7e0a7be4dd4457c99da60d09cb113ab
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731448

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