Methanol → Methyl 3-fluoro-4-hydroxybenzoate

HRID 404339

Reaktionsgleichung

Reaktionsgleichung von HRID 404339
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH3:17])=[O:6]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1604563-Fluoro-4-hydroxybenzoic acid

Produkt 1

HCID 7019368Methyl 3-fluoro-4-hydroxybenzoateAusbeute 87 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a round bottom flask containing 3-fluoro-4-hydroxybenzoic acid (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (5.03 g, 32.22 mmol) was added a cold solution of MeOH (50.0 mL) and sulfuric acid (2.0 mL). The mixture was heated to 80° C. and monitored with TLC. After 20.5 hours, the solvent was removed and the resulting mixture was diluted with diethyl ether. The organic phase was washed carefully two times with saturated aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to afford T10.1 as a white solid (4.79 g, 87% yield). 1H NMR (400 MHz, CDCl3) 7.81 (2H, m), 7.06 (1H, t, J=8.4 Hz), 5.62 (1H, d, J=4.3 Hz), 3.91 (3H, s).

Aufarbeitung

  1. customthe solvent was removed
  2. additionthe resulting mixture was diluted with diethyl ether
  3. washThe organic phase was washed carefully two times with saturated aqueous NaHCO3
  4. dry with materialonce with brine, and then dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe organic solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-337ee80103ea4c7fba08271b9b856f9c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748462B2

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