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

HRID 1414130

Reaction equation

HRID 1414130 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-8b7d9eb93d28423c9fd5364a70e94154
Source dataset
uspto-grants-1981_02
Patent number
US04252979

Linked notes

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