Thionyl Chloride → 2-Propynoyl chloride

HRID 1441153Notes

Reaction equation

HRID 1441153 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:15]([O-])(=[O:18])[C:16]#[CH:17].[Na+].S(Cl)(Cl)=O.[C:25]([Cl:29])(=[O:28])[C:26]#[CH:27]>C1C=CC=CC=1>[C:25]([Cl:29])(=[O:28])[C:26]#[CH:27].[C:15]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:18])[C:16]#[CH:17]

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 615235-Phenyl-1-pentanolHCID 4314123propiolic acid, sodium saltHCID 122606682-Propynoyl chloride

Product 2

HCID 122606682-Propynoyl chlorideHCID 189814815-Phenylpentyl propiolate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent4×

Procedure

With stirring, 1 gram of 5-phenylpentanol was added dropwise to a mixture of 0.25 g of sodium hydride (60% oil suspension) and 25 ml of dried benzene. The mixed solution is further stirred at ambient temperatures for one hour. A benzene solution of propiolic acid chloride is prepared by stirring a mixture of 0.62 g of sodium propiolate, 0.80 g of thionyl chloride, and 20 ml of dried benzene at ambient temperatures for five hours. The benzene solution of propiolic acid chloride thus prepared is added to the mixed solution, stirred at ambient temperatures for five hours, and refluxed for one hour. After the reaction is completed, the reaction solution is washed successively with water and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained residue is subjected to silicagel column chromatography to yield 5-phenylpentyl propiolate (compound 1).

Workup

  1. stirringThe mixed solution is further stirred at ambient temperatures for one hour
  2. stirringby stirring
  3. additionis added to the mixed solution
  4. stirringstirred at ambient temperatures for five hours
  5. temperaturerefluxed for one hour
  6. washthe reaction solution is washed successively with water
  7. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  8. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1c3d68f2142e4ab181486f06fd3e2a66
Source dataset
uspto-grants-1996_03
Patent number
US05502242

Reaction notes

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