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

HRID 617836

Reaction equation

HRID 617836 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-73c4a82ac4f2473c9c3df8f241921ac9
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Linked notes

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