Thionyl Chloride → HCID 20291112, compound

HRID 1413867Notes

Reaction equation

HRID 1413867 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:22]([O-:24])=[O:23])[C:5]([OH:21])=[C:6]([CH:8](O)[C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([N+:16]([O-:18])=[O:17])[C:10]=2[OH:19])[CH:7]=1.S(Cl)([Cl:27])=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:22]([O-:24])=[O:23])[C:5]([OH:21])=[C:6]([CH:8]([Cl:27])[C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([N+:16]([O-:18])=[O:17])[C:10]=2[OH:19])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53898321HCID 53898321, compound

Product 1

HCID 20291112HCID 20291112, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of bis(5-chloro-2-hydroxy-3-nitrophenyl)methyl alcohol (4.5 g) and thionyl chloride (50 ml) was heated under reflux for 3 hr. Dimethylformamide (0.1 g) was added to the reaction mixture and the mixture was heated under reflux for a further hour. Excess thionyl chloride was then removed by distillation under reduced pressure and the remaining red oil was crystallised from ethanol to give 4 g of bis(5-chloro-2-hydroxy-3-nitrophenyl)methyl chloride, m.p. 180° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further hour
  5. customExcess thionyl chloride was then removed by distillation under reduced pressure
  6. customthe remaining red oil was crystallised from ethanol

Sources & evidence

ORD record
ord-28246f1650cb44d99921ab080cebd835
Source dataset
uspto-grants-1981_02
Patent number
US04251546

Reaction notes

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