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

HRID 2309031Notes

Reaction equation

HRID 2309031 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][S:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]O)=[CH:9][CH:8]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:5][S:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][Cl:3])=[CH:9][CH:8]=1

Participants

5

Reactant 2

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

Product 1

HCID 701281-(Chloromethyl)-4-(methylthio)benzeneYield 88.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of thionyl chloride (47.6 g) in methylene chloride is slowly added to a solution of 4-(methylthio)benzyl alcohol (50.0 g) in pyridine (37.2 g) such that the temperature never exceeds 25° C. After the addition is complete the mixture is stirred an additional 2 hours at room temperature, then washed with water, dried, and the solvents removed. The resulting red oil is mixed with hexane which is decanted and evaporated to give 49.6 g of 4-(methylthio)benzyl chloride as a yellow oil, suitable for use in the reaction described next below.

Workup

  1. additionAfter the addition
  2. washwashed with water
  3. customdried
  4. customthe solvents removed
  5. additionThe resulting red oil is mixed with hexane which
  6. customis decanted
  7. customevaporated

Sources & evidence

ORD record
ord-3cddbaef9b2345bb83502460fe2f16ea
Source dataset
uspto-grants-1987_09
Patent number
US04692448

Reaction notes

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