4-Toluenesulfonyl chloride → p-Toluenesulfonic acid 1-butyn-3-yl ester

HRID 1648427Notes

Reaction equation

HRID 1648427 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH3:12][CH:13]([OH:16])[C:14]#[CH:15].[OH-].[K+]>CCOCC>[S:1]([O:16][CH:13]([C:14]#[CH:15])[CH3:12])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 162393-Butyn-2-ol

Product 1

HCID 561098p-Toluenesulfonic acid 1-butyn-3-yl esterYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of tosyl chloride (0.5 mole) and commercial 3-butyn-2-ol (0.4 mole 40-50% aqueous solution) in ether (350 ml), potassium hydroxide (2.5 moles) is slowly added over a period of 15-30 minutes. The temperature is maintained at 0°-5° C. for the entire period and the reaction mixture is allowed to stand for 90 minutes. When the reaction is complete, the ether phase is washed and dried. Removal of the ether, in vacuo, yields crude 2-tosyloxy-3-butyne.

Workup

  1. temperatureThe temperature is maintained at 0°-5° C. for the entire period
  2. washthe ether phase is washed
  3. customdried
  4. customRemoval of the ether

Sources & evidence

ORD record
ord-d6422958a27749808aa9847924fa9c83
Source dataset
uspto-grants-1995_07
Patent number
US05436273

Reaction notes

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