Benzene → 2-Benzyloxyethyl propiolate

HRID 1441152Notes

Reaction equation

HRID 1441152 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12](O)(=[O:15])[C:13]#[CH:14].C1C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:15])[C:13]#[CH:14]

Participants

6

Reactant 3

HCID 241BenzeneHCID 10110Propiolic AcidHCID 121412-(Benzyloxy) ethanol

Product 1

HCID 189814822-Benzyloxyethyl propiolateYield 89.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A mixture of 2 g of 2-benzyloxyethanol, 2.8 g of propiolic acid, 0.005 g of p-toluenesulfonic acid and 25 ml of benzene was refluxed with stirring for six hours while water formed was removed by a Dean-Stark water separator. After the reaction was completed, the reaction solution was washed successively with a 5% aqueous sodium bicarbonate solution and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained residue was subjected to silicagel column chromatography to yield 2.39 g of 2-benzyloxyethyl propiolate (compound 16).

Workup

  1. temperaturewas refluxed
  2. customformed
  3. customwas removed by a Dean-Stark water separator
  4. washthe reaction solution was washed successively with a 5% aqueous sodium bicarbonate solution
  5. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8d7e984abc3a4e89ba23ed23d4ffd0ac
Source dataset
uspto-grants-1996_03
Patent number
US05502242

Reaction notes

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