Thionyl Chloride → 1-Chloro-1-decene

HRID 1086975Notes

Reaction equation

HRID 1086975 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][CH:10]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 2

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

Product 1

HCID 537900151-Chloro-1-deceneYield 95.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

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 mixture was added dropwise 24.0 g of thionyl chloride, during cooling with ice. After dropping thionyl chloride, reaction was carried out for 8.5 hours at 70° C. After conclusion of the reaction, the reaction solution was diluted with dichloromethane, and then washed with an aqueous potassium carbonate. The washed solution was dried on magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain 27.7 g of 1-chloro-1-decene. (Yield: 95%)

Workup

  1. customthe mixture was placed into an eggplant flask
  2. temperatureduring cooling with ice
  3. customAfter conclusion of the reaction
  4. washwashed with an aqueous potassium carbonate
  5. customThe washed solution was dried on magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-d03ce15cfd7b404c9d3a39b87788b163
Source dataset
uspto-grants-1991_07
Patent number
US05034153

Reaction notes

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