Benzaldehyde → alpha-Ethynylbenzenemethanol

HRID 659139

Reaktionsgleichung

Reaktionsgleichung von HRID 659139
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([Mg]Br)#[CH:10].[Cl-].[NH4+]>C1COCC1.C(OCC)C>[C:2]1([CH:1]([OH:8])[C:9]#[CH:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 240Benzaldehyde2×HCID 25517Ammonium ChlorideHCID 178418486HCID 178418486, Verbindung

Produkt 1

HCID 20155alpha-Ethynylbenzenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2.65 g of benzaldehyde (Formula 26) in 50 mL of THF at room temperature was added 100 mL of 0.5M ethynylmagnesium bromide in THF. The mixture was stirred at room temperature for 2 hours. Then, the mixture was diluted with diethylether and a saturated solution of ammonium chloride. The mixture was extracted with ethyl acetate. Combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (20% ethyl acetate/hexane) gave 3.17 g of 1-phenyl-prop-2-yn-1-ol (Formula 27) as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ 2.68 (m, 1H), 5.46-5.49 (m, 1H), 7.34-7.43 (m, 3H), 7.55-7.57 (m, 2H).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. washCombined ethyl acetate was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-54eda138bf08464bbbf77e5d0f0fbb67
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080570B2

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