2-Hydroxy-p-toluic acid → Methyl 2-methoxy-4-methylbenzoate

HRID 59313

Reaktionsgleichung

Reaktionsgleichung von HRID 59313
[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[C:12]([O-])([O-])=O.[K+].[K+].CI.CN([CH:23]=[O:24])C>>[CH3:12][O:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:24][CH3:23])=[O:5]

Komponenten

5

Edukt 4

HCID 57882-Hydroxy-p-toluic acidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Produkt 1

HCID 7172021Methyl 2-methoxy-4-methylbenzoate

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-hydroxy-4-methylbenzoic acid (10.00 g, 65 mmol) in DMF (10 mL) was added K2CO3 (13.6 g, 98 mmol). The reaction mixture was stirred at 60° C. for 1 h. Methyl iodide (14.0 g, 98 mmol) was added to the reaction mixture and was stirred at 60° C. for 18 h. The reaction mass was quenched in water and concentrated. The reaction mass was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 10.00 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 2.34 (s, 3H), 3.74 (s, 3H), 3.79 (s, 3H), 6.81 (d, J=7.2 Hz, 1H), 6.97 (s, 1H), 7.56 (d, J=7.8 Hz, 1H); MS (m/z): 180.95 (M+H)+.

Aufarbeitung

  1. stirringwas stirred at 60° C. for 18 h
  2. customThe reaction mass was quenched in water
  3. concentrationconcentrated
  4. extractionThe reaction mass was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a779c0a97d594d48bc1125917c241a90
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439890B2

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