alpha-Ethynylbenzenemethanol → 3-Oxo-3-phenylpropyne

HRID 1448166

Reaktionsgleichung

Reaktionsgleichung von HRID 1448166
[C:1]1([CH:7]([OH:10])[C:8]#[CH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(C)=O.O.S(=O)(=O)(O)O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]1([C:7]([C:8]#[CH:9])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 1

HCID 20155alpha-Ethynylbenzenemethanol

Produkt 1

HCID 771793-Oxo-3-phenylpropyne

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10219390chromium (VI) trioxideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of 1-phenyl-2-propyne-1-ol (34.2 g) in 50 ml acetone is cooled down to 0°, stirred under N2 and treated dropwise, over a period of 3 hours with a solution of chromium trioxide (17.5 g) in water (50 ml) and concentrated sulfuric acid (14.8 ml), keeping the temperature below 5° at all times. After the addition is complete, the mixture is stirred for another hour at 5°. The reaction mixture is then diluted with water (100 ml) and extracted with two 250-ml portions of ether. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and stripped to give a yellow product. A small amount dried on a porous plate gives a m.p. of 45°-47°.

Aufarbeitung

  1. customthe temperature below 5°
  2. additionAfter the addition
  3. stirringthe mixture is stirred for another hour at 5°
  4. extractionextracted with two 250-ml portions of ether
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customto give a yellow product
  8. customA small amount dried on a porous plate
  9. customgives a m.p. of 45°-47°

Quellen und Nachweise

ORD-Eintrag
ord-33925942a52f43e99342a2b6c8baa298
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04179561

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