Methylphenylacetylene → Diphenylacetylene

HRID 879942Notes

Reaction equation

HRID 879942 reaction equation
[C:1]1([C:7]#[C:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(C)C=CC=CC=1>[C:1]1([C:7]#[C:8][C:9]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 69601Methylphenylacetylene

Product 1

HCID 10390DiphenylacetyleneYield 78.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

In a dry 10 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3(phen)].0.5 toluene (58.8.0 μmol, 68.3 mg) and dried CuCl2 (58.8 μmol, 7.9 mg) were suspended in 2.5 mL of toluene. After addition of 1-phenyl-1-propine (588 μmol, 68.3 mg), the reaction solution was stirred for 24 h at 80° C. and was filtered after cooling over a short silica gel column (2 cm). The filtrate was concentrated and the residue was purified by column chromatography (hexane). 41.0 mg of tolane (78%) were isolated as a white solid, the spectroscopic and analytical data of which were identical to those of a commercial sample. M.p.=59-61° C.

Workup

  1. filtrationwas filtered
  2. temperatureafter cooling over a short silica gel column (2 cm)
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography (hexane)

Sources & evidence

ORD record
ord-0c34e50491d8489eafdc99de8d5770ca
Source dataset
uspto-grants-2015_03
Patent number
US08993470B2

Reaction notes

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