4-Toluenesulfonyl chloride → (3-Chloroprop-1-yn-1-yl)benzene

HRID 617836

Reaktionsgleichung

Reaktionsgleichung von HRID 617836
[C:1]1([C:7]#[C:8][CH2:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S([Cl:21])(C1C=CC(C)=CC=1)(=O)=O>N1C=CC=CC=1>[C:1]1([C:7]#[C:8][CH2:9][Cl:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 1231153-Phenyl-2-propyn-1-ol

Produkt 1

HCID 287343(3-Chloroprop-1-yn-1-yl)benzeneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1-Phenyl-1-propyn-3-ol (5 g), 5.1 g of tosyl chloride and 20 ml of pyridine were stirred at room temperature for 1 hour. The reaction mixture was poured into 100 ml of ice water and extracted with ethyl acetate. The oil layer was washed with 1 N hydrochloric acid and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away. The residue was purified by silica gel column chromatography (ethyl acetate:hexane 1:5) to give 2.54 g of 3-phenyl-2-propynyl chloride as a pale yellow, oily substance.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe oil layer was washed with 1 N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane 1:5)

Quellen und Nachweise

ORD-Eintrag
ord-73c4a82ac4f2473c9c3df8f241921ac9
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952316

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