Thionyl Chloride → 2,4-Dihydroxy-5-nitrobenzoyl chloride

HRID 643931

Reaction equation

HRID 643931 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:17])=O>CN(C)C=O>[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([Cl:17])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 166379152,4-Dihydroxy-5-nitrobenzoic acid

Product 1

HCID 866240182,4-Dihydroxy-5-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 2,4-dihydroxy-5-nitrobenzoic acid (14.2 g, 92.1 mmol), thionyl chloride (100 mL, 1.15 mol) and dimethylformamide (4 drops) is refluxed for 4 h. The solvents are removed under reduced pressure and the resulting gum is stripped once with toluene and dried under reduced pressure to afford 2,4-dihydroxy-5-nitrobenzoyl chloride as a gum, which is used without further purification.

Workup

  1. temperatureis refluxed for 4 h
  2. customThe solvents are removed under reduced pressure
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-b7dd4120b87a494dbb01e675fd858e3c
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Linked notes

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