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

HRID 2083106Notes

Reaction equation

HRID 2083106 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-phenoxyhexane 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. Boiling point0.5 : 117° - 120° C.

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
  8. custom117° - 120° C.

Sources & evidence

ORD record
ord-8f7b55bb3ecb4d3ba29fd66b34a5ecf5
Source dataset
uspto-grants-1978_04
Patent number
US04083990

Reaction notes

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