Hydroquinone → 2,2'-Propane-1,3-diyldipyridine

HRID 1926490Notes

Reaction equation

HRID 1926490 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[CH2:9].[Na].C1(C=CC(O)=CC=1)O>O>[CH2:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:9][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 75212-VinylpyridineHCID 79752-MethylpyridineHCID 5360545Sodium

Product 1

HCID 3221312,2'-Propane-1,3-diyldipyridineYield 18.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask were added 93 g of 2-picoline, 21 g of 2-vinylpyridine, 1 g of sodium and a trace of hydroquinone. The mixture was heated to 130 C under nitrogen for 2 hours. After cooling to 22 C, 200 ml of water were added and the mixture was extracted with 150 ml diethyl ether. After washing the diethyl ether layer twice with 100 ml of water, and twice with 50 ml of 10% sodium sulfite, the solvent was removed and the product was purified by vacuum distillation to give 7.5 g of a light yellow oil.

Workup

  1. temperatureThe mixture was heated to 130 C under nitrogen for 2 hours
  2. additionwere added
  3. extractionthe mixture was extracted with 150 ml diethyl ether
  4. washAfter washing the diethyl ether layer twice with 100 ml of water
  5. customtwice with 50 ml of 10% sodium sulfite, the solvent was removed
  6. distillationthe product was purified by vacuum distillation

Sources & evidence

ORD record
ord-195f8527a4db43139692a1b1e2ae54aa
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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