Thionyl Chloride → 10-Chloro-1-decene

HRID 2352586Notes

Reaction equation

HRID 2352586 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

Reactant 2

HCID 24386Thionyl Chloride2×HCID 256129-Decen-1-ol

Product 1

HCID 1174513910-Chloro-1-deceneYield 95.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

10 drops of pyridine was added to 26.0 g of 9-decene-1-ol and the mixture was placed in an eggplant type flask. Into the flask was then dropped 24.0 g of thionyl chloride while cooling with ice. After dropping thionyl chloride, reaction was carried out for 8.5 hours at 70° C. After the reaction, the resulting reaction solution was diluted with dichloromethane and was washed with an aqueous potassium hydroxide solution. The organic phase was dried over magnesium sulfate and was then 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 in an eggplant type flask
  2. temperaturewhile cooling with ice
  3. customAfter the reaction
  4. customthe resulting reaction solution
  5. washwas washed with an aqueous potassium hydroxide solution
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. concentrationwas then concentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-756996190d1a437cae52fdab262cc154
Source dataset
uspto-grants-1989_10
Patent number
US04877858

Reaction notes

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