Benzophenone → alpha,alpha-Diphenyl-4-pyridinemethanol

HRID 1736649Notes

Reaction equation

HRID 1736649 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.C1(C)C(C)=CC=CC=1.[Na]>O>[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

6

Reactant 4

HCID 3102BenzophenoneHCID 7237O-XyleneHCID 75064-CyanopyridineHCID 5360545Sodium

Product 1

HCID 74177alpha,alpha-Diphenyl-4-pyridinemethanolYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL RB flask were charged 4-cyanopyridine (10.4 g, 0.1 mole) and benzophenone (18.2 g, 0.1 mole). To this, xylene (250 mL) and sodium metal (5.0 g, 0.22 mole) cut into small pieces were added. The flask was heated slowly and refluxed under an inert atmosphere (e.g. nitrogen) with magnetic stirring for 3 hours. The color of the reaction mixture changed from clear to dark blue to dark brown during this time. The reaction mixture was cooled to room temperature and water was carefully added (150 mL). The solid product was filtered and washed with water and acetone. 4-Pyridyl diphenyl carbinol (18.3 g, 70% yield) was thus recovered with m.p. 238°-240° C.

Workup

  1. additionwere added
  2. temperatureThe flask was heated slowly
  3. temperaturerefluxed under an inert atmosphere (e.g. nitrogen)
  4. filtrationThe solid product was filtered
  5. washwashed with water and acetone

Sources & evidence

ORD record
ord-67ab34d20cea493d953cd9b0f7c7cdfc
Source dataset
uspto-grants-1996_07
Patent number
US05541331

Reaction notes

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