Water → alpha,alpha-Diphenyl-4-pyridinemethanol

HRID 1736651Notes

Reaction equation

HRID 1736651 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].C([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)#N.O>C1(C)C(C)=CC=CC=1>[N:21]1[CH:22]=[CH:23][C:18]([C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[OH:8])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3102BenzophenoneHCID 75064-CyanopyridineHCID 5360545Sodium

Product 1

HCID 74177alpha,alpha-Diphenyl-4-pyridinemethanolYield 93.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

Benzophenone (54.6 grams, 0.3 mole) was charged into a 1 liter roundbottom three neck flask equipped with a mechanical stirrer, reflux condenser and dropping funnel. Xylene (300 ml) and sodium metal (16.6 grams, 0.72 mole) cut into small pieces were then added. The flask was heated slowly and refluxed under an inert atmosphere (nitrogen) with mechanical stirring for 30 minutes. 4-cyanopyridine (38.2 grams, 0.37 mole) dissolved in xylene (200 ml) was then added over a period of 1 hour, whereafter the mixture was refluxed for an additional three hours. The reaction mixture was then cooled to room temperature and water (300 ml) was carefully added. The solid was then filtered and washed with water and acetone to give 4-pyridyl diphenyl carbinol (73.1 grams, 93% yield)

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. additionwere then added
  4. temperatureThe flask was heated slowly
  5. temperaturerefluxed under an inert atmosphere (nitrogen)
  6. additionwas then added over a period of 1 hour, whereafter the mixture
  7. temperaturewas refluxed for an additional three hours
  8. filtrationThe solid was then filtered
  9. washwashed with water and acetone

Sources & evidence

ORD record
ord-980b54bfef79403ca0139d3d1f54b8cd
Source dataset
uspto-grants-1996_07
Patent number
US05541331

Reaction notes

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