Acetic Acid → 1-(4-Ethynylphenyl)ethan-1-one

HRID 1477235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1477235
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1)(C)C.[OH-].[K+].CC(O)=O>CO>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1)#[CH:5]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 11746050Ethanone, 1-[4-[(trimethylsilyl)ethynyl]phenyl]-

Produkt 1

HCID 51236261-(4-Ethynylphenyl)ethan-1-oneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a stirring solution of compound 1.9 (19 g, 88 mmol) in MeOH (200 mL) was added a solution of KOH (2.46 g, 44 mmol) in MeOH (20 mL) at 10° C. and the mixture was stirred at room temperature for 1 hr. AcOH was added until the pH was 7, and the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL), washed with 5% aqueous NaHCO3 (100 mL), brine (100 mL), dried, and concentrated under reduced pressure to give compound 1.10 as a white solid (12 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ 7.95 (d, J=8, 2H), 7.62 (d, J=8, 2H), 4.49 (s, 1H), 2.59 (s, 3H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with 5% aqueous NaHCO3 (100 mL), brine (100 mL)
  4. customdried
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-472a892854d6416ebc9ff2b2d52c43b7
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403758B2

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