Benzene → 7-Phenylheptyl propiolate

HRID 1441150Notes

Reaction equation

HRID 1441150 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](O)(=[O:18])[C:16]#[CH:17].C1C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:15]([O:14][CH2:13][CH2:12][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

6

Reactant 3

HCID 241BenzeneHCID 10110Propiolic AcidHCID 154271Benzeneheptanol

Product 1

HCID 153350297-Phenylheptyl propiolateYield 57.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.5 g of 7-phenylheptanol, 0.27 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 0.368 g of 7-phenylheptyl propiolate (compound 3).

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-592b17591caf497c8005c5364b9aa64b
Source dataset
uspto-grants-1996_03
Patent number
US05502242

Reaction notes

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