Methanol → di-p-tolylbutadiyne

HRID 1700824Notes

Reaction equation

HRID 1700824 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[CH:8])=[CH:3][CH:2]=1.CO>Cl[Cu].N1C=CC=CC=1>[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:8]#[C:7][C:4]2[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 13018p-Ethynyltoluene

Product 1

HCID 3336004di-p-tolylbutadiyneYield 69%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1049PyridineSolvent

Procedure

In a 100 mL round bottom flask equipped with a gas inlet tube, was placed a Teflon covered magnetic stirring bar, p-tolylacetylene (5.0 g, 43 mmol), methanol 5 mL, pyridine 1.25 mL, and CuCl (0.2 g, 2 mmol). The reaction mixture was vigorously stirred while air was bubbled through it (A. Vogel, Vogel's Textbook of Practical Organic Chemistry, 4th Ed. Longman, London, England, 1978, p 351) Concentrated HCl (2 mL) and saturated sodium chloride (10 mL) was added. The precipitate was isolated by filtration. It was washed with water, dried, and recrystallized from toluene to give 3.45 g, 69% yield, mp 181-183° C. (Lit, 183° C. (Kunckell, Chem. Zentralblatt, 1913, I,1768)). 1H NMR δ: 7.40(d, 4H, J=8.25 Hz), 7.12(d, 4K J=8.25 Hz), 2.35(s, 6H)

Workup

  1. customIn a 100 mL round bottom flask equipped with a gas inlet tube
  2. customwas bubbled through it (A
  3. additionLongman, London, England, 1978, p 351) Concentrated HCl (2 mL) and saturated sodium chloride (10 mL) was added
  4. customThe precipitate was isolated by filtration
  5. washIt was washed with water
  6. customdried
  7. customrecrystallized from toluene
  8. customto give 3.45 g, 69% yield, mp 181-183° C. (Lit, 183° C. (Kunckell, Chem. Zentralblatt, 1913, I,1768))

Sources & evidence

ORD record
ord-5f609f2da0ec478a99270bf432edbc38
Source dataset
uspto-grants-2002_02
Patent number
US06350875B1

Reaction notes

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