Thionyl Chloride → 3,5-Dichlorobenzyl chloride

HRID 235006

Reaction equation

HRID 235006 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-bdb0d67da7534dafb0fa57d272a144a0
Source dataset
uspto-grants-1997_01
Patent number
US05597828

Linked notes

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