Hydrochloric Acid → 4-But-2-ynyloxy-benzenethiol

HRID 278332Notes

Reaction equation

HRID 278332 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=O)=O)=[CH:27][CH:26]=1)[C:21]#[C:22][CH3:23].Cl>C(Cl)Cl.CN(C=O)C.[Cl-].[Na+].O>[CH2:20]([O:24][C:25]1[CH:26]=[CH:27][C:28]([SH:31])=[CH:29][CH:30]=1)[C:21]#[C:22][CH3:23]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

Product 1

HCID 235138844-But-2-ynyloxy-benzenethiolYield 58%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 11.8 g (0.045 mol) of triphenylphosphine in 10 mL of CH2Cl2 and 0.3 mL of DMF was added dropwise a solution of 4-but-2-ynyloxy-benzenesulfonyl chloride in 15 mL CH2Cl2. Stirred at room temperature for two hours, added 5 mL of 1N HCl, stirred for 30 min., and then added 15 mL of brine. The organics were separated and concentrated in vacuo. The residue was diluted with ether and filtered the insolubles. The filtrate was washed with 2.5N NaOH and the aqueous solution separated, acidified and extracted with ether. The organics were washed with H2O, brine, dried over MgSO4, filtered and concentrated in vacuo to give 1.54 g (58%) of the desired product as a pale yellow oil.

Workup

  1. stirringstirred for 30 min.
  2. customThe organics were separated
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ether
  5. filtrationfiltered the insolubles
  6. washThe filtrate was washed with 2.5N NaOH
  7. customthe aqueous solution separated
  8. extractionextracted with ether
  9. washThe organics were washed with H2O, brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be90a3eb1dcd46d29ae5931f1c66d78c
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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