Thionyl Chloride → 1-(2-Chloroethoxy)-4-nitrobenzene

HRID 430961Notes

Reaction equation

HRID 430961 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12]O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:16])=O>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][Cl:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 853812-(4-Nitrophenoxy)ethanol

Product 1

HCID 27645871-(2-Chloroethoxy)-4-nitrobenzene

Procedure

4-Nitro-(2-Hydroxyethoxy)benzene (1.13 g, 6.2 mmol) in thionyl chloride (10 mL) is heated at reflux for 3 hours then concentrated in vacuo . After cooling the residue in an ice water bath, saturated aqueous sodium bicarbonate is added and the precipitate collected, rinsed with water, and dried to give 4-nitro-(2-chloroethoxy)benzene (909 mg).

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationthen concentrated in vacuo
  3. temperatureAfter cooling the residue in an ice water bath
  4. additionsaturated aqueous sodium bicarbonate is added
  5. customthe precipitate collected
  6. washrinsed with water
  7. customdried

Sources & evidence

ORD record
ord-ea144ce9af6f4ab7930e7ca0a4d7b999
Source dataset
uspto-grants-2003_12
Patent number
US06656941B2

Reaction notes

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