Sodium Hydroxide → 2-(4-Fluoro-2-methylphenoxy)-2-methylpropanoic acid

HRID 1876397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876397
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10]CC)=[O:9])=[C:4]([CH3:17])[CH:3]=1.[OH-].[Na+]>O1CCCC1.CO.O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]([CH3:14])([CH3:13])[C:8]([OH:10])=[O:9])=[C:4]([CH3:17])[CH:3]=1

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 67405334Ethyl 2-(4-fluoro-2-methylphenoxy)-2-methylpropanoate

Produkt 1

HCID 585663572-(4-Fluoro-2-methylphenoxy)-2-methylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-fluoro-2-methylphenol (10 g, 79.28 mmol), ethyl 2-bromoisobutyrate (23.2 mL, 158.6 mmol), potassium carbonate (21.9 g, 158.6 mmol), and DMSO (80 mL) was stirred at room temperature for 72 hours. Water and ethyl acetate were added and the layers were separated. The aqueous phase was extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (20%) to afford ethyl 2-(4-fluoro-2-methylphenoxy)-2-methylpropanoate. To a solution of ethyl 2-(4-fluoro-2-methylphenoxy)-2-methylpropanoate (13.3 g, 55.44 mmol) in tetrahydrofuran (40 mL) and methanol (10 mL) was added NaOH (6.66 g, 166.32 mmol) in water (14 mL) and stirred overnight. The volatiles were removed in vacuo and acidified with concentrated HCl. The milky white solution was extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated in vacuo to give 2-(4-fluoro-2-methylphenoxy)-2-methylpropanoic acid (658) as a yellow solid.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. extractionThe milky white solution was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-762646cd8ef042f986f365bbf1faa13e
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309600B2

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