Thionyl Chloride → 10-Chloro-1-decene

HRID 1199866Notes

Reaction equation

HRID 1199866 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].S(Cl)([Cl:14])=O>N1C=CC=CC=1.ClCCl>[Cl:14][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10]

Participants

5

Procedure

To 26.0 g of 9-decene-1-ol was added 10-drops of pyridine and the mixture was placed into an eggplant flask. To the eggplant flask was added dropwise 24.0 g of thionyl chloride during cooling with ice. After dropping, the mixture was reacted for 8.5 hours at 70° C. After the conclusion of the reaction, the reaction product was diluted with dichloromethane and then washed with an aqueous potassium carbonate solution. The reaction solution was then dried over magnesium sulfate and subsequently concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain 27.7 g of 10-chloro-1-decene. (Yield: 95%)

Workup

  1. customthe mixture was placed into an eggplant flask
  2. temperatureduring cooling with ice
  3. customthe mixture was reacted for 8.5 hours at 70° C
  4. customAfter the conclusion of the reaction
  5. washwashed with an aqueous potassium carbonate solution
  6. dry with materialThe reaction solution was then dried over magnesium sulfate
  7. concentrationsubsequently concentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-f1bc5469004c4bc2ac4b6826801d7aaa
Source dataset
uspto-grants-1990_02
Patent number
US04904065

Reaction notes

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