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

HRID 839836Notes

Reaction equation

HRID 839836 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 b 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-f700654fedbb472dbde439accd7a2995
Source dataset
uspto-grants-1978_06
Patent number
US04097496

Reaction notes

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