Thionyl Chloride → o-Tolyl 2-methoxy-3-chloromethylphenyl thioether

HRID 1164109Notes

Reaction equation

HRID 1164109 reaction equation
[CH3:1][O:2][C:3]1[C:10]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]O.S(Cl)([Cl:21])=O>N1C=CC=CC=1.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH2:5][Cl:21])=[CH:7][CH:8]=[CH:9][C:10]=1[S:11][C:12]1[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 545312442-Methoxy-3-(o-tolylthio)benzyl alcohol

Product 1

HCID 20513475o-Tolyl 2-methoxy-3-chloromethylphenyl thioether

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 2-methoxy-3-(o-tolylthio)benzyl alcohol (8.5 g), thionyl chloride (4.8 ml) and pyridine (3 drops) in benzene (80 ml) was stirred at room temperature and then at 80° C. for 10 minutes. The reaction mixture was treated in a similar manner to that of Example 21-(6) to give oily o-tolyl 2-methoxy-3-chloromethylphenyl thioether (8.3 g).

Workup

  1. additionThe reaction mixture was treated in a similar manner to that of Example 21-(6)

Sources & evidence

ORD record
ord-64b00faca09a4b24b115632615958d21
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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