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

HRID 919007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919007
[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-131b977081b844c4b5201471ca299196
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09272986B2

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