Methanol → 4-Ethynylbenzoic acid

HRID 928911

Reaktionsgleichung

Reaktionsgleichung von HRID 928911
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si](C)(C)C)=[CH:6][CH:5]=1.CO>[OH-].[K+]>[C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:16])=[O:2])=[CH:5][CH:6]=1)#[CH:11]

Komponenten

4

Edukt 2

HCID 887MethanolHCID 640161Methyl 4-trimethylsilylethynylbenzoate

Produkt 1

HCID 5897064-Ethynylbenzoic acidAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14797Potassium HydroxideLösungsmittel

Versuchsvorschrift

4-(Trimethylsilyl)ethynyl-benzoic acid methyl ester (714 mg, 3.07 mmol) was dissolved in 4% KOH:MeOH (w:v, 30 mL) and allowed to reflux overnight. The reaction was quenched with 6N HCl to pH 2-3 (as indicated by pH paper) and extracted 2× with EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and evaporated to afford 4-ethynylbenzoic acid (427 mg, 2.92 mmol, 95%) as a brown solid. H-NMR (d6-acetone, 500 MHz) δ (ppm): 7.62 (d, J=16.2 Hz, 2H); 8.03 (d, J=16.3 Hz, 2H).

Aufarbeitung

  1. temperatureto reflux overnight
  2. customThe reaction was quenched with 6N HCl to pH 2-3 (as indicated by pH paper)
  3. extractionextracted 2× with EtOAc
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-98662fcbbfb745b18b974dd42668d863
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290791B2

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