Thionyl Chloride → 1-Chloromethyl-3-methylsulfanylbenzene

HRID 2414247Notes

Reaction equation

HRID 2414247 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH2:9]O)[CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:13])=O>C1C=CC=CC=1>[Cl:13][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([S:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 122557423-(Methylthio)benzyl alcohol

Product 1

HCID 110628871-Chloromethyl-3-methylsulfanylbenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (3-methylsulfanyl-phenyl)-methanol (23.8 g, 0.156 mol) in benzene (250 mL) was added thionyl chloride (26.9 g, 0.234 mol) under cooling with an ice-bath. The ice-bath was removed and the reaction mixture stirred for 48 hours at room temperature. The solution was concentrated and used without further work-up (26.9 g).

Workup

  1. temperatureunder cooling with an ice-bath
  2. customThe ice-bath was removed
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-a340bec19a314daca7a0487ea3cc4a67
Source dataset
uspto-grants-2004_11
Patent number
US06812228B2

Reaction notes

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