Sodium Benzoate → Ethynyl benzoate

HRID 1975549Notes

Reaction equation

HRID 1975549 reaction equation
FC(F)(F)S([O-])(=O)=O.[C:9]([I+]C1C=CC=CC=1)#[CH:10].[C:18]([O-:26])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na+]>C(Cl)Cl.O>[C:18]([O:26][C:9]#[CH:10])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 517055Sodium BenzoateHCID 10959799Ethynyl(phenyl)iodonium trifluoromethanesulfonate

Product 1

HCID 15632868Ethynyl benzoateYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethynyl(phenyl)iodonium trifluoromethanesulfonate (3.78 grams, 10 millimoles) dissolved in 10 milliliters of methylene chloride was mixed with sodium benzoate (7.2 grams, 50 millimoles) dissolved in 20 milliliters of water. The reactants were stirred for 5 minutes at 0° C. The organic layer was concentrated by evaporation and chromatographed on silica gel columns to isolate 0.77 grams of ethynyl benzoate (53% yield). The product was identified by spectroscopic means, and had a melting point of 43° C.(dec).

Workup

  1. concentrationThe organic layer was concentrated by evaporation
  2. customchromatographed on silica gel columns

Sources & evidence

ORD record
ord-d745dfee426f4c99bbade341def0d98b
Source dataset
uspto-grants-1994_02
Patent number
US05286901

Reaction notes

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