Benzophenone → alpha,alpha-Diphenyl-4-pyridinemethanol

HRID 1736653Notes

Reaction equation

HRID 1736653 reaction equation
[Na].[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)#N.C(C1C=CC=CN=1)#N>C1(C)C(C)=CC=CC=1.O>[N:21]1[CH:22]=[CH:23][C:18]([C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[OH:9])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 3102Benzophenone3×HCID 75064-CyanopyridineHCID 7522Pyridine-2-carbonitrile2×HCID 5360545Sodium

Product 1

HCID 74177alpha,alpha-Diphenyl-4-pyridinemethanolYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent2×

Procedure

Sodium (16.6 grams, 0.72 mole) metal and xylene (150 ml) were charged into a 1 liter round bottom three-neck flask equipped with a mechanical stirrer, reflux condenser and two dropping funnels. The mixture was brought to reflux and the addition of benzophenone (54.6 grams, 0.3 mole) was begun. When about 1/4 to 1/3 of the benzophenone had added during 15-30 minutes, the addition of a solution of 4-cyanopyridine (38.2 grams, 0.37 mole) in xylene (200 mL) was begun at a rate so that about 1/2 of the cyanopyridine solution had been added when the addition of benzophenone was complete. The remaining cyanopyridine solution was added during another 30 minutes. Upon work-up with water (300 mL), 4-pyridyl diphenyl carbinol was obtained in about 95% yield.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureto reflux
  4. additionhad been added when

Sources & evidence

ORD record
ord-ab9c08ad6313455086533a6792ce6632
Source dataset
uspto-grants-1996_07
Patent number
US05541331

Reaction notes

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