Potassium Hydroxide → 1-(3-Methoxyphenyl)-1,3-butadiyne

HRID 1614379Notes

Reaction equation

HRID 1614379 reaction equation
OC(C)(C)[C:3]#[C:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1.[OH-].[K+]>C1C=CC=CC=1>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([C:6]#[C:5][C:4]#[CH:3])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 197738166-(3-Methoxyphenyl)-2-methylhexa-3,5-diyn-2-ol

Product 1

HCID 197738141-(3-Methoxyphenyl)-1,3-butadiyneYield 73.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

800 mg of the thus-obtained diacetylene compound were dissolved in 200 ml of benzene, and 300 mg of potassium hydroxide were added to the reaction mixture, followed by reflux under heating for 15 minutes. After filtration, the solvent was evaporated, and the residue was purified by silica-gel chromatography using as hexane as an eluent to obtain 430 mg of 1-(3-methoxyphenyl)-1,3-butadiyne.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 15 minutes
  3. filtrationAfter filtration
  4. customthe solvent was evaporated
  5. customthe residue was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-cbd123f1c6e64fad99f6a40332116714
Source dataset
uspto-grants-1993_03
Patent number
US05196586

Reaction notes

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