Methanol → 4-(Methoxycarbonyl)-2-nitrobenzoic acid

HRID 1451112

反応式

HRID 1451112 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH3:21]O>>[CH3:21][O:14][C:13]([C:11]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=1)=[O:15]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 691221,4-Benzenedicarboxylic acid, 2-nitro-

生成物 1

HCID 219064744-(Methoxycarbonyl)-2-nitrobenzoic acid収率 55%

実験手順

A mixture of nitroterephthalic acid (Aldrich, 20 g, 0.095 mol) in anhydrous methanol (100 mL) was heated to reflux in the presence of concentrated sulphuric acid (10 mL) for 1 h. The solvent was evaporated and the residue poured into saturated sodium bicarbonate (200 mL). The aqueous layer was washed with chloroform and 2N hydrochloric acid added to the aqueous layer to bring the pH close to 2. The mixture was extracted twice with ethyl acetate and the combined organic layers were washed with water and brine. The organic extract was concentrated after drying over sodium sulphate and the residue was recrystallized from ethyl acetate-hexane to give 11.8 g (55%) of 4-methoxycarbonyl-2-nitrobenzoic acid as cream-colored crystals, mp 131°-132° C.

後処理

  1. temperaturewas heated
  2. customThe solvent was evaporated
  3. additionthe residue poured into saturated sodium bicarbonate (200 mL)
  4. washThe aqueous layer was washed with chloroform and 2N hydrochloric acid
  5. additionadded to the aqueous layer
  6. customclose to 2
  7. extractionThe mixture was extracted twice with ethyl acetate
  8. washthe combined organic layers were washed with water and brine
  9. extractionThe organic extract
  10. concentrationwas concentrated
  11. dry with materialafter drying over sodium sulphate
  12. customthe residue was recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-15bbe074cb3942beb3690da0d7287911
出典データセット
uspto-grants-1997_02
特許番号
US05602277

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