Thionyl Chloride → 2-Chlorophenyl 2-methoxy-3-chloromethylphenyl thioether

HRID 1164080Notes

Reaction equation

HRID 1164080 reaction equation
[CH3:1][O:2][C:3]1[C:10]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]O.S(Cl)([Cl:21])=O>N1C=CC=CC=1.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH2:5][Cl:21])=[CH:7][CH:8]=[CH:9][C:10]=1[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 53999561HCID 53999561, compound

Product 1

HCID 205134642-Chlorophenyl 2-methoxy-3-chloromethylphenyl thioether

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 2-methoxy-3-(2-chlorophenylthio)benzyl alcohol (9 g), thionyl chloride (4.6 ml) and pyridine (3 drops) in dried benzene (60 ml) was refluxed under heating for 30 minutes. The reaction mixture was cooled to the ambient temperature and evaporated under reduced pressure. The residue was dissolved in diethyl ether, and the solution was washed with water, saturated aqueous sodium bicarbonate and water in turn, dried over magnesium sulfate and then evaporated under reduced pressure to give oily 2-chlorophenyl 2-methoxy-3-chloromethylphenyl thioether (9.2 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 30 minutes
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washthe solution was washed with water, saturated aqueous sodium bicarbonate and water in turn
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ee3ee6d3e94e4c04bc8dd8a29e34a833
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

Loading…