4-Toluenesulfonyl chloride → Iodopropargyl 4methylbenzenesulfonate

HRID 1707732Notes

Reaction equation

HRID 1707732 reaction equation
[I:1][CH:2]([OH:5])[C:3]#[CH:4].[OH-].[Na+].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C1COCC1.O>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:5][CH:2]([I:1])[C:3]#[CH:4])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 602749Iodopropargyl alcohol

Product 1

HCID 18321752Iodopropargyl 4methylbenzenesulfonateYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 500 mL 4-neck round bottom flask, equipped with a magnetic stirrer and an addition funnel, in an ice bath were placed iodopropargyl alcohol (10 g, 54.9 mmol) in THF (20 mL) and sodium hydroxide (3.4 g, 84.6 mmol) in water (20 mL) To the above cold mixture was added a solution of p-toluenesulfonyl chloride (10.4 g, 54.95 mmol) in THF (20 mL) from an addition funnel. The reaction mixture was stirred for 2 hrs. below 5° C. The reaction mixture was then poured into ice water and the precipitate was collected by suction-filtration and washed with water. After drying under vacuum, the precipitate afforded 17.2 g (yield: 93.4%) of iodopropargyl 4methylbenzenesulfonate as an off-white solid, mp=75°-78 ° C. An NMR spectrum showed the desired compound.

Workup

  1. customInto a 500 mL 4-neck round bottom flask, equipped with a magnetic stirrer and an addition funnel, in an ice bath
  2. custombelow 5° C
  3. filtrationthe precipitate was collected by suction-filtration
  4. washwashed with water
  5. customAfter drying under vacuum

Sources & evidence

ORD record
ord-f4540bce37fd44068fb0339b5d7f80b7
Source dataset
uspto-grants-1994_10
Patent number
US05354862

Reaction notes

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