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

HRID 1416954Notes

Reaction equation

HRID 1416954 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:13])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 592968[4-(Methylsulfanyl)phenyl]methanol

Product 1

HCID 701281-(Chloromethyl)-4-(methylthio)benzeneYield 90.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 50.0 g (325 mMol) of 4-(methylthio)benzyl alcohol in 350 ml of toluene stirring at room temperature under nitrogen, was added 5 drops of pyridine, and then 28.4 ml (46.4 g, 390 mMol, 1.2 eqs) of thionyl chloride was added dropwise. After 3 hours, ice water was added and the mixture was stirred for 20 minutes. The mixture was transferred to a separatory funnel and shaken thoroughly. The organic layer separated and was dried over sodium sulfate, filtered, and evaporated. Distillation of the residue under reduced pressure gave (4-methylthiophenyl)chloromethane (50.54 g) as a colorless liquid: b.p. 89-95° C. (1 mm).

Workup

  1. customThe mixture was transferred to a separatory funnel
  2. stirringshaken thoroughly
  3. customThe organic layer separated
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-10998cc714bf48078586794e7799f5b3
Source dataset
uspto-grants-1999_06
Patent number
US05916905

Reaction notes

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