Thionyl Chloride → 2-(3-Cyclohexylpropyloxy)-ethyl chloride

HRID 1388152Notes

Reaction equation

HRID 1388152 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:16])=O>N1C=CC=CC=1>[CH:1]1([CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][Cl:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 204717772-(3-Cyclohexylpropyloxy)-ethanol

Product 1

HCID 204717382-(3-Cyclohexylpropyloxy)-ethyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

110.4 g of 2-(3-cyclohexylpropyloxy)-ethanol, 2 ml of pyridine and 112 ml of thionyl chloride are boiled under reflux for 30 minutes. The reaction mixture is allowed to cool and is then poured onto 500 g of ice. The mixture is extracted with twice 500 ml of methylene chloride. The combined organic phases are washed with water, with sodium hydrogen carbonate solution, with water again and are then concentrated. The residue is distilled. 119.6 g of 2-(3-cyclohexylpropyloxy)-ethyl chloride are obtained [bp 68°-69° C. at 0.01 mm Hg (1.3 Pa)].

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureto cool
  3. extractionThe mixture is extracted with twice 500 ml of methylene chloride
  4. washThe combined organic phases are washed with water, with sodium hydrogen carbonate solution, with water again
  5. concentrationare then concentrated
  6. distillationThe residue is distilled

Sources & evidence

ORD record
ord-5bf151aaaf534be189e4e1e52b38d5a4
Source dataset
uspto-grants-1984_02
Patent number
US04430339

Reaction notes

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