Methanol → 5-(Methoxycarbonyl)-2-methylbenzoic acid

HRID 397238

Reaktionsgleichung

Reaktionsgleichung von HRID 397238
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].S(Cl)(Cl)=O.N1C=CC=C[CH:19]=1.CO>CN(C=O)C.C(Cl)(Cl)(Cl)Cl>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([C:11]([OH:13])=[O:12])[CH:4]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 5957504-Methylbenzene-1,3-dicarboxylic acid

Produkt 1

HCID 229994865-(Methoxycarbonyl)-2-methylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of compound (2) (2.83 g, 15.71 mmol), thionyl chloride (50 ml) and DMF (3 drops) was heated at reflux for 2 hours. After cooling to room temperature, excess thionyl chloride was removed under reduced pressure (rotary evaporator). The dark oil which was obtained was dissolved in carbon tetrachloride (30 ml), treated with pyridine (1 ml, 12.43 mmol) and methanol (20 ml) and stirred at ambient temperature for 2 hours. The solvents were evaporated and the residue purified by flash chromatography: silica, hexane/EtOAc (9:1).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customexcess thionyl chloride was removed under reduced pressure (rotary evaporator)
  4. customThe dark oil which was obtained
  5. customThe solvents were evaporated
  6. customthe residue purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3c7986863cd943adb62352da01f11da9
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610269B1

Verknüpfte Notizen

Wird geladen…