Hydrochloric Acid → 4-(2-(4-Methylphenyl)ethynyl)benzaldehyde

HRID 2287923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2287923
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[CH:8].Cl.CN(C)[CH:13]=[O:14]>[Cu](I)I>[CH3:7][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:7][C:2]2[CH:1]=[CH:6][C:5]([CH:13]=[O:14])=[CH:4][CH:3]=2)=[CH:6][CH:1]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 1365982-Methylphenylacetylene

Produkt 1

HCID 112414734-(2-(4-Methylphenyl)ethynyl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 83717Copper iodideKatalysator

Versuchsvorschrift

According to the method of J. Cole et al., J. Chem. Soc., 244 (1962), a mixture of toluylacetylene (200 mmol), 2-(4-bromophenyl)-1,3-dioxalane (200 mmol), dimethylformamide (500 ml), and copper iodide (I) (300 mmol) was heated while stirring for 5 hours. After allowed to cool, 500 ml of 6M hydrochloric acid was added and stirred for 1 hour. It was extracted with 500 ml of toluene, and the organic layer was washed with water thrice and dried with anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by a silica gel column chromatography (eluent:toluene) to obtain 120 mmol of 4-(2-(4-methylphenyl)ethynyl)benzaldehyde.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto cool
  3. stirringstirred for 1 hour
  4. extractionIt was extracted with 500 ml of toluene
  5. washthe organic layer was washed with water thrice
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by a silica gel column chromatography (eluent:toluene)

Quellen und Nachweise

ORD-Eintrag
ord-40bee8814a3a4107b5bb69e72d3db924
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06086964

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