p-Toluenesulfonic acid → 7-Phenylheptyl propiolate

HRID 1441156Notes

Reaction equation

HRID 1441156 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].[C:8]1([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]CCO)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:1]([O:5][CH2:6][CH2:7][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:4])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12182Ethyl propiolateHCID 154271Benzeneheptanol

Product 1

HCID 153350297-Phenylheptyl propiolate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1 g of ethyl propiolate, 2.94 g of 7-phenylheptanol and 0.01 g of p-toluenesulfonic acid in 30 ml of benzene was refluxed for twelve hours. After removal of the solvent under reduced pressure, the obtained residue was subjected to silicagel column chromatography to yield 7-phenylheptyl propiolate (compound 3).

Workup

  1. temperaturewas refluxed for twelve hours
  2. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8f00825490dc4b71ad8a3d5f6965a0bc
Source dataset
uspto-grants-1996_03
Patent number
US05502242

Reaction notes

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