Diethyl Ether → 4-Vinylbenzoic acid

HRID 428782

Reaktionsgleichung

Reaktionsgleichung von HRID 428782
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[OH-].[Na+].C(OCC)C>C1COCC1.O>[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 583124Methyl 4-ethenylbenzoate

Produkt 1

HCID 140984-Vinylbenzoic acidAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a well-stirred solution of methyl p-vinylbenzoate (36.0 g, 0.222 mole) in THF (200 mL) was added a solution of sodium hydroxide (17.78 g, 0.444 mole) in water (200 mL) at room temperature. After stirring overnight, water (100 mL), THF (150 mL), and ethyl ether (200 mL) was added and the phases separated. The aqueous phase was acidified with a solution of concentrated hydrochloric acid (41 mL) in water (90 mL) then extracted three times with THF (500-600 mL each). The latter combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to provide 32.7 g (99.5 percent) of white solids. Proton nmr (Gemini model 300 MHz) in deuterochloroform: delta 8.08 (2H), 7.50 (2H), 6.78 (1H), 5.90 (1H), 5.41 (1H).

Aufarbeitung

  1. customthe phases separated
  2. extractionthen extracted three times with THF (500-600 mL each)
  3. dry with materialThe latter combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0aeeedd0afab4e92ac9a1d754d9a4439
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313340B1

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