Sulfuric Acid → 1,4-Diphenyl-1,3-butadiyne

HRID 1646150

Reaction equation

HRID 1646150 reaction equation
C(O[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][C:13]=1F)CCCCCCCCC.S(=O)(=O)(O)O>N1C=CC=CC=1.CO>[CH:12]1[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:19]#[C:18][C:15]2[CH:14]=[CH:13][CH:12]=[CH:17][CH:16]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 146182651-(Decyloxy)-4-ethynyl-2-fluorobenzene

Product 1

HCID 701741,4-Diphenyl-1,3-butadiyneYield 225.9%

Reagents, catalysts & solvents 1

HCID 22021344Pyridine methanolSolvent

Procedure

To a 50 ml round bottom flask equipped with a magnetic stirrer and reflux condenser was added 300 mg 4-decyloxy-3-fluorophenylacetylene and 43 mg cupric acetate in 40 ml 1:1 pyridine/MeOH. The reaction mixture was refluxed for 2 hrs, allowed to cool to room temperature and then added dropwise into a stirred 9 M aqueous sulfuric acid solution at ice bath temperature. The resulting cream-like suspension was extracted with ethyl ether and sequentially washed with water (3x) and brine and dried with anhydrous magnesium sulfate yielding 289 mg of a yellow-brown solid. Flash chromatography (1% ethyl acetate/hexane) and recrystallization of the residue from 95% ethanol afforded 248 mg diphenyldiacetylene (V), 4,4'-didecyloxy-3,3'-difluoro diphenyldiacetylene, as pale yellow needles.

Workup

  1. customTo a 50 ml round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was refluxed for 2 hrs
  4. extractionThe resulting cream-like suspension was extracted with ethyl ether
  5. washsequentially washed with water (3x) and brine
  6. dry with materialdried with anhydrous magnesium sulfate yielding 289 mg of a yellow-brown solid
  7. customFlash chromatography (1% ethyl acetate/hexane) and recrystallization of the residue from 95% ethanol

Sources & evidence

ORD record
ord-b953cacb95fb49c589bf02db153921f6
Source dataset
uspto-grants-1993_01
Patent number
US05178791

Linked notes

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