Thionyl Chloride → 3,5-Dichlorobenzyl chloride

HRID 846369Notes

Reaction equation

HRID 846369 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5]O.S(Cl)([Cl:13])=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5][Cl:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 432363,5-Dichlorobenzylic alcohol

Product 1

HCID 1378803,5-Dichlorobenzyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,5-dichlorobenzyl alcohol (Aldrich, 25 g), thionyl chloride (100 ml) and DMF (0.5 ml) was stirred and refluxed for 4 hours. After cooling the mixture was concentrated in vacuo, the residue was taken up in ether, washed with saturated aqueous NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to give 3,5-dichlorobenzyl chloride as a light yellow solid, which was used without further purification, 28 g, mp. 32°-36° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureAfter cooling the mixture
  3. concentrationwas concentrated in vacuo
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-223af8dc4cd24e67a5a00b26ba19af31
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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