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

HRID 1970690Notes

Reaction equation

HRID 1970690 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-caeb3ed8d3394b8aacba0085e087886e
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

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