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

HRID 1058147Notes

Reaction equation

HRID 1058147 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-dc7885dbe5c941e5b8faade83c4084ad
Source dataset
uspto-grants-2003_02
Patent number
US06515140B2

Reaction notes

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