Pyridine → Benzyl 2-Chloroethyl Ether

HRID 344287Notes

Reaction equation

HRID 344287 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:20])=O>ClCCl>[CH2:1]([O:8][CH2:9][CH2:10][Cl:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 121412-(Benzyloxy) ethanolHCID 24386Thionyl Chloride

Product 1

HCID 223538Benzyl 2-Chloroethyl Ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-benzyloxyethanol (11.7 g) and pyridine (6.08 g) in dichloromethane (50 ml) was added thionyl chloride (6.7 ml) under ice-cooling, and the resulting mixture was stirred at refluxing temperature for 2.5 hr. Ice-water was added to the reaction mixture, and the organic layer was washed with water and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform) to give 10.3 g of 2-benzyloxyethyl chloride.

Workup

  1. temperaturecooling
  2. temperatureat refluxing temperature for 2.5 hr
  3. washthe organic layer was washed with water
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-87e6a2a00ff7458f97067897a8383f92
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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