Benzophenone → alpha,alpha-Diphenyl-4-pyridinemethanol

HRID 1736650Notes

Reaction equation

HRID 1736650 reaction equation
C([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#N.[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[N:6]1[CH:7]=[CH:8][C:3]([C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:16])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 3102BenzophenoneHCID 75064-Cyanopyridine

Product 1

HCID 74177alpha,alpha-Diphenyl-4-pyridinemethanol

Procedure

To a 3-necked 500 mL RB flask fitted with a mechanical stirrer were charged 4-cyanopyridine (10.4 g, 0.1 mole) and benzophenone (18.2 g, 0.1 mole). Dry liquid ammonia was carefully added (250 mL) and the starting materials were dissolved. Sodium metal was then added (5.0 g, 0.22 mole) slowly in small pieces. The reaction mixture was stirred for 1 hour and the ammonia allowed to evaporate. Toluene (150 mL) and water (150 mL) were then added to the residue and the resulting mixture was stirred for 15 minutes. The precipitated product was filtered and washed with water, giving 4-pyridyl diphenyl carbinol.

Workup

  1. customTo a 3-necked 500 mL RB flask fitted with a mechanical stirrer
  2. dry with materialDry liquid ammonia
  3. additionwas carefully added (250 mL)
  4. dissolutionthe starting materials were dissolved
  5. additionSodium metal was then added (5.0 g, 0.22 mole) slowly in small pieces
  6. customto evaporate
  7. additionToluene (150 mL) and water (150 mL) were then added to the residue
  8. stirringthe resulting mixture was stirred for 15 minutes
  9. filtrationThe precipitated product was filtered
  10. washwashed with water

Sources & evidence

ORD record
ord-af4395b45ade4253b2702070ff798bf2
Source dataset
uspto-grants-1996_07
Patent number
US05541331

Reaction notes

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