Thionyl Chloride → 1-Chloro-2-methyl-6-phenoxy-hexane

HRID 1287354Notes

Reaction equation

HRID 1287354 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH:7]([CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl.CN(C=O)C>[Cl:3][CH2:6][CH:7]([CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 203221341-Hydroxy-2-methyl-6-phenoxyhexane

Product 1

HCID 203221511-Chloro-2-methyl-6-phenoxy-hexane

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 60 g of thionyl chloride in 50 ml of CHCl3 was added dropwise to 100 g of 1-Hydroxy-2-methyl-6-phenoxy-hexane in 200 ml of CHCl3 and 0.5 ml of DMF. The solution was refluxed until the development of the gas was finished and then poured onto ice. The aqueous phase was extracted twice with CHCl3 and the combined organic phases were washed with water and finally with a saturated NaHCO3 -solution, dried with MgSO4, evaporated and the residue was distilled off.

Workup

  1. temperatureThe solution was refluxed until the development of the gas
  2. additionpoured onto ice
  3. extractionThe aqueous phase was extracted twice with CHCl3
  4. washthe combined organic phases were washed with water and finally with a saturated NaHCO3 -solution
  5. dry with materialdried with MgSO4
  6. customevaporated
  7. distillationthe residue was distilled off

Sources & evidence

ORD record
ord-0c447d406cfd4a7695fa61ca2c9da751
Source dataset
uspto-grants-1976_10
Patent number
US03984459

Reaction notes

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