Methylphenylacetylene → Diphenylacetylene

HRID 879945Notes

Reaction equation

HRID 879945 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 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a dry 25 mL Schlenk-tube, which has been flooded with argon, [Mo(≡N)(OSiPh3)3)(bipy)] (109.2 mg, 0.10 mmol), MnCl2 (12.6 mg, 0.10 mmol) and molecular sieve 5 Å (1.0 g) was suspended in dry toluene (5 mL) and the mixture was heated to 80° C. After 30 min, 1-phenyl-1-propine (116.2 mg, 1.00 mmol) was added, the reaction mixture was stirred for 3 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by means of column chromatography (hexane). 88.2 mg of tolane (99%) were isolated as a white solid, the spectroscopic and analytical data 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
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by means of column chromatography (hexane)

Sources & evidence

ORD record
ord-eda6176aa82f44ac8a729ac8e5b7cd31
Source dataset
uspto-grants-2015_03
Patent number
US08993470B2

Reaction notes

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