m-Chloroperbenzoic acid → HCID 57027781, compound

HRID 362262Notes

Reaction equation

HRID 362262 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:20][C:21]#[C:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:15][CH:14]=1>ClCCl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:20][C:21]#[C:22][CH2:23][O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:6])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12197679HCID 12197679, compound

Product 1

HCID 57027781HCID 57027781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperoxybenzoic acid (55% purity; 81 g) in dichloromethane (1400 ml) was added dropwise over 2.5 hours to a stirred, ice-cold solution of the crude 1-(4-chlorophenylthio)-4-phenoxybut-2-yne (74.5 g) in dichloromethane (600 ml), then the mixture was stirred at ambient temperature for 18 hours and filtered. The filtrate was washed with 5% aqueous sodium carbonate solution (3×750 ml) and water (3×500 ml) then dried (Na2SO4), and the solvent removed in vacuo. The residue was dissolved in hot dichloromethane (40 ml), then petroleum ether (b.p. 60°-80° C.) (75 ml) was added, and the mixture was triturated to give a sticky solid which was collected by filtration, triturated with hot ether (500 ml), collected by filtration, and dried in vacuo to give 1-(4-chlorophenylsulphinyl)-4-phenoxybut-2-yne as a solid (21.73 g), m.p. 102°-103° C.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 5% aqueous sodium carbonate solution (3×750 ml) and water (3×500 ml)
  3. dry with materialthen dried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was dissolved in hot dichloromethane (40 ml)
  6. additionpetroleum ether (b.p. 60°-80° C.) (75 ml) was added
  7. customthe mixture was triturated
  8. customto give a sticky solid which
  9. filtrationwas collected by filtration
  10. customtriturated with hot ether (500 ml)
  11. filtrationcollected by filtration
  12. customdried in vacuo

Sources & evidence

ORD record
ord-bcb1be72296e457a876c59b72450b2a5
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Reaction notes

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