Lithium Hydroxide → 4-Bromo-3-(butyloxy)benzoic acid

HRID 1662335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662335
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8]CCCC)=[O:7])=[CH:4][C:3]=1[O:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[Li+]>C1COCC1.CO>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:15][CH2:16][CH2:17][CH2:18][CH3:19]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 57467609Butyl 4-bromo-3-(butyloxy)benzoate

Produkt 1

HCID 577062304-Bromo-3-(butyloxy)benzoic acidAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a solution of 5.1 (0.90 g, 2.7 mmol) in THF/MeOH (2/1) (18 mL), was added lithium hydroxide (6.0 mL, 6.0 mmol). The resulting mixture was stirred overnight at 23° C. and then quenched with excess 1N HCl. The mixture was then extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The crude residue was purified by combiflash (0 to 40% EtOAc/hexanes) to afford a 20.1 (0.68 g, 91% yield).

Aufarbeitung

  1. customquenched with excess 1N HCl
  2. extractionThe mixture was then extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by combiflash (0 to 40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-62afdeecd4c1410f8709478fd2dffb27
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

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