Sodium Hydroxide → 1-(4-Ethynylphenyl)ethan-1-one

HRID 1095234

Reaktionsgleichung

Reaktionsgleichung von HRID 1095234
C[C:2]1[C:3](C)=[C:4]([C:11]#[C:12]CO)[CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH3:9].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([C:11]#[CH:12])=[CH:3][CH:2]=1)(=[O:10])[CH3:9]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66784133HCID 66784133, Verbindung

Produkt 1

HCID 51236261-(4-Ethynylphenyl)ethan-1-oneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

1.45 g (7.17 mmol) of dimethylhydroxymethyl-4-acetylphenylacetylene and 301 mg (7.53 mmol) of NaOH (KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98%) were placed in a 100 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 36 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 15 minutes. 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. Then, 25 mL of hexane was added to the resulting crude reaction product and the mixture was cooled to give 4-acetylphenylethyne as a yellow solid. (0.74 g, yield: 56%).

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. additionThen, 25 mL of hexane was added to the resulting crude
  6. customreaction product
  7. temperaturethe mixture was cooled

Quellen und Nachweise

ORD-Eintrag
ord-51a39bf682344d698bde5af78593cdee
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08137821B2

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