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Sodium Hydroxide → 3'-Fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

HRID 2410473
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2410473
[OH-].[Na+].[F:3][C:4]1[C:5]([CH3:23])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][C:11]=2[CH2:20][O:21][CH3:22])[CH:7]=[CH:8][CH:9]=1>CCO>[F:3][C:4]1[C:5]([CH3:23])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][C:11]=2[CH2:20][O:21][CH3:22])[CH:7]=[CH:8][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 58554131Methyl 3'-fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylate

Produkt 1

HCID 580663983'-Fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A 5 N aqueous solution of NaOH (5.0 mL, 25 mmol) was added into a solution of methyl 3′-fluoro-2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate (4.85 g, 16.8 mmol) in EtOH (50 mL). The reaction mixture was heated at 60° C. for 1 hour, and then was concentrated under reduced pressure. The residue was taken up with MTBE (100 mL), water (50 mL) and a 5N aqueous solution of HCl (6 mL). The layers were separated and the organic layer was washed with water (50 mL) and brine (50 mL). The aqueous layers were extracted with MTBE (50 mL). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. After purification by crystallization from a mixture of MTBE and pentane, the title compound was obtained as a white powder (3.85 g, 83%). HPLC (Method A), Rt 4.2 min (purity: 99.8%). LC/MS (Method B) 273.0. (M−H)−.

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure
  2. customThe layers were separated
  3. washthe organic layer was washed with water (50 mL) and brine (50 mL)
  4. extractionThe aqueous layers were extracted with MTBE (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customAfter purification
  8. customby crystallization
  9. additionfrom a mixture of MTBE and pentane

Quellen und Nachweise

ORD-Eintrag
ord-8fb727ef87074b5ba1e36b8b342dac56
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08815919B2

Notizen zur Reaktion

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