Réaction #95826

ord-0ec63cb2ac29482b80b5b588b7bbf034

Équation de réaction

[O]=[Mn](=[O])(=[O])[O-]
permanganate
Cc1c(F)cccc1[N+](=O)[O-]
6-fluoro-2-nitrotoluene
O=C([O-])[O-].[K+].[K+]
potassium carbonate
[K+].[O]=[Mn](=[O])(=[O])[O-]
potassium permanganate
→
O=C(O)c1c(F)cccc1[N+](=O)[O-]
6-fluoro-2-nitrobenzoic acid

Réactifs

[O]=[Mn](=[O])(=[O])[O-]
permanganate
Cc1c(F)cccc1[N+](=O)[O-]
6-fluoro-2-nitrotoluene
O=C([O-])[O-].[K+].[K+]
potassium carbonate
[K+].[O]=[Mn](=[O])(=[O])[O-]
potassium permanganate

Réactifs

Aucun

Solvants

O
water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autre(ca 2.5 hours)
  2. 2
    TempératureAfter cooling
  3. 3
    Autreremoval of the unreacted 6-fluoro-2-nitrotoluene
  4. 4
    Extractionby extraction with ethyl acetate
  5. 5
    Extractionextracted three times with ethyl acetate
  6. 6
    SéchageThe combined organic extracts are dried over magnesium sulphate
  7. 7
    Concentrationconcentrated

Mode opératoire

A mixture of 34.5 g (0.22 mol) of 6-fluoro-2-nitrotoluene, 30.7 g (0.22 mol) of potassium carbonate, 105.4 g (0.66 mol) of potassium permanganate and 3.3 liters of water is heated at 100° C. until the permanganate is decolorised (ca 2.5 hours). After cooling and removal of the unreacted 6-fluoro-2-nitrotoluene by extraction with ethyl acetate, the aqueous phase is adjusted to pH 1 with hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts are dried over magnesium sulphate and concentrated, there being obtained 6-fluoro-2-nitrobenzoic acid. After recrystallisation from ethyl acetate/n-hexane, the product melts at 146°-148° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04346035uspto-grants-1982_08