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

HRID 37151Notes

Reaction equation

HRID 37151 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

Thus obtained 1-hydroxymethyl-3-methyl-4-phenylthiobenzene was dissolved in 100 ml of methylene chloride, and 23.34 ml of thionyl chloride was added while ice-cooling and stirring. After stirring for 1 hour, the reaction mixture was washed with ice water (100 ml×3), and 500 ml of ethyl acetate was added. The mixture was sequentially washed with 5% aqueous solution of sodium hydrogencarbonate (50 ml×4) and saturated brine (100 ml×2), and dried with anhydrous sodium sulfate, concentrated in vacuo, and 1-chloromethyl-3-methyl-4-phenylthiobenzene was obtained.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 1 hour
  3. washthe reaction mixture was washed with ice water (100 ml×3), and 500 ml of ethyl acetate
  4. additionwas added
  5. washThe mixture was sequentially washed with 5% aqueous solution of sodium hydrogencarbonate (50 ml×4) and saturated brine (100 ml×2)
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f0d05924a8941d8a85b14f6ed4a3fe3
Source dataset
uspto-grants-1995_05
Patent number
US05420128

Reaction notes

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