Sodium Hydroxide → 4-Benzoylphenylethyne

HRID 1095232

Reaktionsgleichung

Reaktionsgleichung von HRID 1095232
C[C:2]1[C:3](C)=[C:4]([C:16]#[C:17]CO)[CH:5]=[CH:6][C:7]=1[C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:8]([C:7]1[CH:2]=[CH:3][C:4]([C:16]#[CH:17])=[CH:5][CH:6]=1)(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66784736HCID 66784736, Verbindung

Produkt 1

HCID 121320044-BenzoylphenylethyneAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

1.85 g (7 mmol) of dimethylhydroxymethyl-4-benzoylphenylacetylene and 294 mg (7.35 mmol) of NaOH (KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98%) were placed in a 50 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 35 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 0.5 hour. Toluene was added to the reaction mixture and the mixture was washed with a saturated aqueous ammonium chloride solution and dried over magnesium sulfate, followed by distilling off of the solvent under reduced pressure by an evaporator. The crude reaction product was purified by column chromatography (Hexane/AcOEt=10/1) using silica gel to give 4-benzoylphenylethyne as a pale brown solid (1.1 g, yield: 76%).

Aufarbeitung

  1. customequipped with a reflux condenser
  2. washthe mixture was washed with a saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationby distilling off of the solvent under reduced pressure by an evaporator
  5. customThe crude reaction product
  6. customwas purified by column chromatography (Hexane/AcOEt=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-4e35b02948d74e6db79e2694cfbf7142
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08137821B2

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