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

HRID 1386648

Reaction equation

HRID 1386648 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-octyn-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-7f8b0d1fb4cf402fa320145c3c12c23a
Source dataset
uspto-grants-2001_07
Patent number
US06265569B1

Linked notes

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