Sodium Hydroxide → 6-Fluoro-4-methoxy-biphenyl-3-carboxylic acid

HRID 2229565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229565
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]([F:13])=[CH:9][C:10]=1[O:11][CH3:12])=[O:4].[OH-].[Na+]>O1CCOCC1>[F:13][C:8]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[C:10]([O:11][CH3:12])[CH:9]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 220934916-Fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester

Produkt 1

HCID 184681996-Fluoro-4-methoxy-biphenyl-3-carboxylic acidAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirring solution of 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester (0.5 g, 2.3 mmol) in dioxane (8 mL, 0.3 M) was added 2N NaOH (6.0 mL, 12 mmol). After one'hour at room temperature, the reaction mixture was concentrated, and 2N HCl was added. The aqueous layer was diluted with ether. The organic layer was separated, dried over Na2SO4, filtered and concentrated to afford a 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid (0.55 g, 96%) as a pale yellow powder: Rf 0.18 (5% methanol in dichloromethane); 1H NMR (CDCl3, 300 MHz) δ 8.35 (d, J=9.0 Hz, 1H), 7.55-7.52 (m, 2H), 7.48-7.38 (m, 3H), 6.89 (d, J=11.7 Hz, 1H), 4.12 (s, 3H).

Aufarbeitung

  1. customAfter one'hour at room temperature
  2. concentrationthe reaction mixture was concentrated
  3. addition2N HCl was added
  4. additionThe aqueous layer was diluted with ether
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d6003dd9e0a94661a2228d60d4c5dee4
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420426B1

Notizen zur Reaktion

Wird geladen…