Thionyl Chloride → 3,5-Dichlorobenzyl chloride

HRID 1081585Notes

Reaction equation

HRID 1081585 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-0e7092bbcf1a4d4bb29c910b74d2b597
Source dataset
uspto-grants-1996_12
Patent number
US05587380

Reaction notes

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