Water → 1-(2-Chloroethoxy)-4-(chloromethyl)benzene

HRID 979785Notes

Reaction equation

HRID 979785 reaction equation
O[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8](CO)=[CH:7][CH:6]=1.[CH:13]([Cl:16])(Cl)Cl.S(Cl)([Cl:19])=O.O>N1C=CC=CC=1>[Cl:19][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:13][Cl:16])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 22256038HCID 22256038, compound

Product 1

HCID 218823281-(2-Chloroethoxy)-4-(chloromethyl)benzeneYield 66.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

10 Grams (0.06 mol) of 4-(2-hydroxyethoxy)benzyl alcohol, prepared according to L. M. Marson, Il Farmaco ed. sci. 14, 159 (1959)), was dissolved in anhydrous pyridine (80 ml) and anhydrous chloroform (100 ml), then the mixture was ice cooled and thionyl chloride (80 ml) was slowly added, under stirring. Stirring was continued, allowing temperature to raise to the room's one, then the mixture was heated for about 2 hours to complete the reaction. After cooling, the reaction mixture was poured into water (200 ml); the chloroformic layer was separated, washed with a 5% aqueous solution of sodium hydroxyde, dried over Na2SO4 and evaporated. The residue was distilled under vacuum to provide the pure product (8.2 g; 66.6% yield).

Workup

  1. temperaturecooled
  2. stirringStirring
  3. temperatureto raise to the room's one
  4. temperaturethe mixture was heated for about 2 hours
  5. customthe reaction
  6. temperatureAfter cooling
  7. customthe chloroformic layer was separated
  8. washwashed with a 5% aqueous solution of sodium hydroxyde
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. distillationThe residue was distilled under vacuum
  12. customto provide the pure product (8.2 g; 66.6% yield)

Sources & evidence

ORD record
ord-0644f79913db457f9b755ff40e63b8cc
Source dataset
uspto-grants-1987_01
Patent number
US04634701

Reaction notes

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