Sulfuric Acid → 3-(Methoxycarbonyl)-5-methylbenzoic acid

HRID 2071122

Reaktionsgleichung

Reaktionsgleichung von HRID 2071122
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14]1COCC1.OS(O)(=O)=O>CO.O>[CH3:14][O:12][C:11]([C:4]1[CH:5]=[C:6]([CH:10]=[C:2]([CH3:1])[CH:3]=1)[C:7]([OH:9])=[O:8])=[O:13]

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 681375-Methylisophthalic acid

Produkt 1

HCID 72108363-(Methoxycarbonyl)-5-methylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To 5-methylisophthalic acid (Aldrich, 5 g, 27.7) in MeOH (37.5 ml)/THF (112.5 ml), conc. H2SO4 (1.25 ml) was added and stirred at 65° C. for 8 h. Reaction mixture was cooled to room temperature and solvent removed. Then reaction mixture was diluted with water and extracted with ethylacetate. Crude residue was column chromatographed to yield 2.5 g of 3-(methoxycarbonyl)-5-methylbenzoic acid as a white solid.

Aufarbeitung

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customsolvent removed
  4. customThen reaction mixture
  5. extractionextracted with ethylacetate
  6. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-485575d1876a408384cb42f3c6a4aacf
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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