Water → Oct-7-yn-1-yl 4-methylbenzene-1-sulfonate

HRID 840053Notes

Reaction equation

HRID 840053 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[CH:19].O>N1C=CC=CC=1>[CH2:12]([O:20][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[CH:19]

Participants

5

Reactant 3

HCID 962Water2×HCID 73974-Toluenesulfonyl chlorideHCID 701007-Octyn-1-ol

Product 1

HCID 10779145Oct-7-yn-1-yl 4-methylbenzene-1-sulfonateYield 85.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
7.5 °C

Procedure

To an ice-cooled solution of p-toluenesulfonyl chloride (17.4 g, 91.3 mmol) in pyridine (30 ml), 7-octyne-1-ol (9.6 g, 76.1 mmol) was added dropwise, and stirred at 5-10 ° C. for 20 hours. The reaction mixture was added with water (15 ml), stirred, then poured into water (500 ml), and extracted with ether (500 ml). The ether layer was washed with cold 1N-hydrochloric acid, saturated aqueous sodium hydrogencarbonate and water, dried over magnesium sulfate, and concentrated under reduced pressure to afford 18.3 g of 7-octynyl-p-toluenesulfonate (yield; 85.7%).

Workup

  1. additionwas added dropwise
  2. stirringstirred
  3. extractionextracted with ether (500 ml)
  4. washThe ether layer was washed with cold 1N-hydrochloric acid, saturated aqueous sodium hydrogencarbonate and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a6fa1f19132a4a20ac9ca491e67428a4
Source dataset
uspto-grants-2002_04
Patent number
US06365350B1

Reaction notes

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