Thionyl Chloride → 1-Chloromethyl-3-methyl-4-phenylthiobenzene

HRID 621640Notes

Reaction equation

HRID 621640 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([CH3:16])[CH:4]=1.S(Cl)([Cl:19])=O>C(Cl)Cl>[Cl:19][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([CH3:16])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19934635HCID 19934635, compound

Product 1

HCID 199346681-Chloromethyl-3-methyl-4-phenylthiobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 1-hydroxymethyl-3-methyl-4-phenylthiobenzene obtained above is dissolved in methylene chloride (100 ml), and thereto is added with stirring thionyl chloride (23.34 ml) under ice cooling. The mixture is stirred for one hour, and the reaction mixture is washed with ice water (100 ml×3), and thereto is added ethyl acetate (500 ml). The mixture is washed in order with 5% aqueous sodium hydrogen carbonate solution (50 ml×4) and saturated aqueous sodium chloride solution (100 ml×2), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1-chloromethyl-3-methyl-4-phenylthiobenzene.

Workup

  1. washthe reaction mixture is washed with ice water (100 ml×3)
  2. additionis added ethyl acetate (500 ml)
  3. washThe mixture is washed in order with 5% aqueous sodium hydrogen carbonate solution (50 ml×4) and saturated aqueous sodium chloride solution (100 ml×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e1f63cb9aee473eb492836264b4855e
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Reaction notes

Loading…