Methanol → Methyl 3,4-Dihydroxy-2-methylbenzoate

HRID 968946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968946
[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([OH:1])[C:3]=1[CH3:12]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 104420733,4-Dihydroxy-2-methylbenzoic acid

Produkt 1

HCID 59016598Methyl 3,4-Dihydroxy-2-methylbenzoateAusbeute 83 %

Versuchsvorschrift

To a round bottom flask equipped with magnetic stirring and a reflux condenser was added 3,4-dihydroxy-2-methylbenzoic acid (23.3 g, 139 mmol), methanol (139 mL), and concentrated sulfuric acid (0.77 mL, 13.9 mmol). This mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature and the methanol evaporated. The residue was taken up in ether and washed once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to give a brown solid, methyl-3,4-dihydroxy-2-methylbenzoate, (20.9 g, 114 mmol) in 83% yield. 1H-NMR (300 MHz, CD3COCD3) δ (ppm): 2.47 (s, 3H), 3.79 (s, 3H), 6.78 (d, 1H), 7.46 (d, 1H); TLC: Rf=0.54 (1:1 ethyl acetate/hexane).

Aufarbeitung

  1. customTo a round bottom flask equipped
  2. temperatureThis mixture was heated
  3. temperatureto reflux for 18 hours
  4. customthe methanol evaporated
  5. washwashed once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cb5448310e50409e934ef002dce9e51b
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304161B2

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