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

HRID 1451575

Reaction equation

HRID 1451575 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 1N 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 1N 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-2be5ba4d22d94bdcac2a7ca824c05221
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Linked notes

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