Thionyl Chloride → 2-Hydroxy-4-nitrobenzoyl chloride

HRID 1910791Notes

Reaction equation

HRID 1910791 reaction equation
S(Cl)([Cl:3])=O.[N+:5]([C:8]1[CH:9]=[C:10]([OH:17])[C:11](=[CH:15][CH:16]=1)[C:12](O)=[O:13])([O-:7])=[O:6]>C(Cl)(Cl)Cl>[OH:17][C:10]1[CH:9]=[C:8]([N+:5]([O-:7])=[O:6])[CH:16]=[CH:15][C:11]=1[C:12]([Cl:3])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 692664-Nitrosalicylic acid

Product 1

HCID 129247202-Hydroxy-4-nitrobenzoyl chlorideYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (1.6 mL, 22 mmol) was added slowly to a solution of 4-nitrosalicylic acid (1.0 g, 5.46 mmol) in chloroform (20 mL) at 0° C. The mixture was brought to reflux and maintained for 5 h. Excess thionyl chloride was evaporated to give 2-hydroxy-4-nitro-benzoyl chloride (0.82 g, 75%).

Workup

  1. temperatureto reflux
  2. temperaturemaintained for 5 h
  3. customExcess thionyl chloride was evaporated

Sources & evidence

ORD record
ord-6a8a671fba7847c0946caa6cb26a9a7d
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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