Potassium Hydroxide → 1-(4-Methoxyphenyl)-1,3-butadiyne

HRID 1614376Notes

Reaction equation

HRID 1614376 reaction equation
OC(C)(C)[C:3]#[C:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[OH-].[K+]>C1C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]#[C:5][C:4]#[CH:3])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 197738155-Hydroxy-5-methyl-1-(4-methoxyphenyl)hexa-1,3-diyne

Product 1

HCID 105111001-(4-Methoxyphenyl)-1,3-butadiyneYield 105.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1500 mg of the diacetylene compound obtained were then dissolved in 300 ml of benzene, and 600 mg of potassium hydroxide, which were finely ground, was then added to the reaction mixture, followed by reflux under heating for 30 minutes. After filtration, the solvent was evaporated, and the residue was then purified by silica-gel chromatrgaphy using hexane as an eluent to obtain 1150 mg of 1-(4-methoxyphenyl)-1,3-butadiyne. This compound was a slightly yellowish white crystal.

Workup

  1. additionwas then added to the reaction mixture
  2. temperatureby reflux
  3. temperatureunder heating for 30 minutes
  4. filtrationAfter filtration
  5. customthe solvent was evaporated
  6. customthe residue was then purified by silica-gel chromatrgaphy

Sources & evidence

ORD record
ord-a19b3ee3f376445fb41e5d74ad14cac1
Source dataset
uspto-grants-1993_03
Patent number
US05196586

Reaction notes

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