Phenylacetylene → Diphenylacetylene

HRID 707211Notes

Reaction equation

HRID 707211 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([C:14]#[CH:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:2]1([C:15]#[C:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 11430Potassium CarbonateHCID 11575Iodobenzene

Product 1

HCID 10390DiphenylacetyleneYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To an ethanol solution (3 ml) containing iodobenzene (102 mg), phenylacetylene (56.1 mg), and potassium carbonate (138 mg) the mesh catalyst precursor (12 mm by 14 mm, wire diameter of 0.1 mm, opening of 0.154 mm) prepared in Example 3 was added to be heated for 12 hours at 80° C. The reaction mixture was cooled to room temperature, and the mesh catalyst precursor was washed with ethanol to be taken off from the mixture. The solvent was distilled away from the reaction mixture under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane) to give an intended product, diphenylacetylene with 15% yield.

Workup

  1. customprepared in Example 3
  2. additionwas added
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washthe mesh catalyst precursor was washed with ethanol
  5. distillationThe solvent was distilled away from the reaction mixture under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (n-hexane)

Sources & evidence

ORD record
ord-bbe8cfe2405e4ad4acd89b7b3fbe60f2
Source dataset
uspto-grants-2015_11
Patent number
US09175004B2

Reaction notes

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