Thionyl Chloride → 1-(Chloromethyl)-4-(phenylthio)benzene

HRID 621637

Reaction equation

HRID 621637 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)=[CH:5][CH:4]=1.S(Cl)([Cl:18])=O>C(Cl)Cl>[Cl:18][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)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 80593p-(Phenylthio)benzyl alcohol

Product 1

HCID 710221-(Chloromethyl)-4-(phenylthio)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 1-hydroxymethyl-4-phenylthiobenzene (3.0 g) is dissolved in methylene chloride (15 ml), and thereto is added with stirring thionyl chloride (1.5 ml) under ice cooling. The mixture is stirred for one hour, and the reaction mixture is washed with ice water (10 ml×3), and thereto is added methylene chloride (50 ml). The mixture is washed in order with 5% aqueous sodium hydrogen carbonate solution (5 ml×3) and saturated aqueous sodium chloride solution (30 ml×2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 1-chloromethyl-4-phenylthiobenzene (3.0 g).

Workup

  1. washthe reaction mixture is washed with ice water (10 ml×3)
  2. additionis added methylene chloride (50 ml)
  3. washThe mixture is washed in order with 5% aqueous sodium hydrogen carbonate solution (5 ml×3) and saturated aqueous sodium chloride solution (30 ml×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9869be6f4db74c7c9036d7efba84631d
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Linked notes

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