Sodium Hydroxide → 2-Fluoro-3-methoxybenzyl alcohol

HRID 729683

Reaktionsgleichung

Reaktionsgleichung von HRID 729683
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].[OH-].[Na+]>CCOCC>[F:7][C:8]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:9]=1[CH2:10][OH:11]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 33906792-Fluoro-3-methoxybenzoic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 5935892-Fluoro-3-methoxybenzyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Lithium aluminium hydride (83.5 ml, 1M solution in THF) was added dropwise to a suspension of the subtitle product of step i) (7.1 g) in Et2O (180 ml) at a rate that maintained gentle reflux. Upon complete addition the reaction was stirred for 1.5 h. 15% sodium hydroxide solution was added dropwise until no effervescence was observed. The resulting white precipitate was filtered and the filtrate diluted with H2O (100 ml). The organics were removed in vacuo and the residue extracted with Et2O (100 ml). The organics were washed with 2M sodium hydroxide solution (150 ml), H2O (150 ml), brine (150 ml), dried (MgSO4) and concentrated in vacuo to afford the subtitle compound as a white crystalline solid. Yield: 5.5 g.

Aufarbeitung

  1. temperaturemaintained gentle reflux
  2. additionUpon complete addition the reaction
  3. filtrationThe resulting white precipitate was filtered
  4. additionthe filtrate diluted with H2O (100 ml)
  5. customThe organics were removed in vacuo
  6. extractionthe residue extracted with Et2O (100 ml)
  7. washThe organics were washed with 2M sodium hydroxide solution (150 ml), H2O (150 ml), brine (150 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-99a4a0b31ebd45bcb5b95228257f91e4
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582644B2

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