Dimethyl Sulfoxide → 2,5-Dichloro-3-nitrobenzoic acid

HRID 1759262

Reaction equation

HRID 1759262 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9](C(O)=O)[C:8]([Cl:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CS(C)=O>>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Cl:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 2809622,5-Dichloro-3-nitrobenzene-1,4-dicarboxylic acid

Product 1

HCID 69512,5-Dichloro-3-nitrobenzoic acid

Procedure

0.05 moles of 2,5-dichloro-3-nitro-terephthalic acid were refluxed in 2.11 moles of dimethyl sulphoxide (DMSO) at 189° C. for 70 minutes, after which the DMSO was removed by flash evaporation. The residue was dissolved in saturated sodium bicarbonate solution, which was extracted with chloroform to remove unwanted side-products. The aqueous phase was then acidified with 10% hydrochloric acid to complete precipitation and the resulting precipitate was filtered off, washed well with water and dried to give 88.5% crude yield of 2,5-dichloro-3-nitro-benzoic acid, melting at 214°-216° C.

Workup

  1. customafter which the DMSO was removed by flash evaporation
  2. dissolutionThe residue was dissolved in saturated sodium bicarbonate solution
  3. extractionwhich was extracted with chloroform
  4. customto remove unwanted side-products
  5. customprecipitation
  6. filtrationthe resulting precipitate was filtered off
  7. washwashed well with water
  8. customdried

Sources & evidence

ORD record
ord-1e79ecc727d345cf963c6db09c33ab85
Source dataset
uspto-grants-1982_07
Patent number
US04339601

Linked notes

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