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

HRID 2393203Notes

Reaction equation

HRID 2393203 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-34fbaad55c9a4cb99c392d27e3dd3b72
Source dataset
uspto-grants-1998_09
Patent number
US05804686

Reaction notes

Loading…