Thionyl Chloride → HCID 19934631, compound

HRID 621633Notes

Reaction equation

HRID 621633 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)=[C:5]([O:16][CH3:17])[CH:4]=1.S(Cl)([Cl:20])=O>C(Cl)Cl>[Cl:20][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)=[C:5]([O:16][CH3:17])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19934719HCID 19934719, compound

Product 1

HCID 19934631HCID 19934631, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 1-hydroxymethyl-3-methoxy-4-phenylthiobenzene obtained above is dissolved in methylene chloride (372 ml), and thereto is added with strring thionyl chloride (9.12 ml) under ice cooling. The mixture is stirred for one hour, and the reaction mixture is washed with ice water (500 ml×2), and thereto is added ethyl acetate (500 ml). The mixture is washed in order with 5% aqueous sodium hydrogen carbonate solution (20 ml), water (200 ml) and saturated aqueous sodium chloride solution (200 ml×2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 1-chloromethyl-3-methoxy-4-phenylthiobenzene.

Workup

  1. washthe reaction mixture is washed with ice water (500 ml×2)
  2. additionis added ethyl acetate (500 ml)
  3. washThe mixture is washed in order with 5% aqueous sodium hydrogen carbonate solution (20 ml), water (200 ml) and saturated aqueous sodium chloride solution (200 ml×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77b86bc514ae4cf7a5fac992f70eaa65
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Reaction notes

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