Thionyl Chloride → 4-(2-Chloroethyl)phenyl methyl ether

HRID 53101

Reaction equation

HRID 53101 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8]O)=[CH:5][CH:4]=1.S(Cl)([Cl:14])=O>ClCCl.[Cl-].[Na+].O>[Cl:14][CH2:8][CH2:7][C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 697054-Methoxyphenethyl alcohol

Product 1

HCID 875134-(2-Chloroethyl)phenyl methyl etherYield 51%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-methoxy-phenethyl alcohol (15.2 g, 10 mmol) were dissolved in 200 ml of dichloromethane and at 0° C., 7.35 ml of thionyl chloride were added. The reaction mixture was allowed to warm to room temperature over 1/2 hour. After stirring for 20 hours, the mixture was added to brine and extracted with dichloromethane. The dichloromethane was evaporated to obtain an oil which was chromatographed on silica gel using a mixture of 30% ethyl acetate/hexane as the eluent to obtain 8.8 g (51%) of the title product.

Workup

  1. extractionextracted with dichloromethane
  2. customThe dichloromethane was evaporated
  3. customto obtain an oil which
  4. customwas chromatographed on silica gel using
  5. additiona mixture of 30% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-3108fabd02d34a17998757fd77927f83
Source dataset
uspto-grants-1997_04
Patent number
US05618793

Linked notes

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