Ammonia → 1,1-diphenyl-2-(pyridin-2-yl)ethanol

HRID 1701177Notes

Reaction equation

HRID 1701177 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.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21].[NH2-].[Li+].N>O>[C:2]1([C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([OH:8])[CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222Ammonia4×HCID 3102BenzophenoneHCID 79752-MethylpyridineHCID 24532Lithium amide

Product 1

HCID 2342681,1-diphenyl-2-(pyridin-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

Benzophenone, 32.4 kg (177.8 mole), α-picoline, 33.1 kg (355.5 moles), and lithium amide, 4.54 kg (197.4 moles) are charged into a 30 gallon reactor arranged for reflux operation. The mixture is stirred, rapidly heated to 125° C. and maintained at this temperature. The rate of ammonia evolution will gradually increase and after about 3 to 4 hours of reaction time only occasional heating is required to maintain the desired temperature and a rapid evolution of ammonia. After about 5 hours, a vigorous surge of ammonia evolution is noted. Following the ammonia surge, external heating is continued and the reaction maintained at 125° C. for an additional 6 to 8 hours. The reaction mixture is cooled to 70°-80° C. and rapidly added to approximately 230 liters of water at 25° C. Stirring is continued for approximately 30 minutes and the solid removed by filtration. The filter cake is thoroughly washed with water and dried at 60° -70° C. yielding 42-6 kg of α,α-diphenyl-2-pyridineethanol having a m.p. of 147°-51° C.

Workup

  1. temperaturefor reflux operation
  2. temperaturemaintained at this temperature
  3. temperatureonly occasional heating
  4. temperatureto maintain the desired temperature
  5. temperatureexternal heating
  6. temperaturethe reaction maintained at 125° C. for an additional 6 to 8 hours
  7. temperatureThe reaction mixture is cooled to 70°-80° C.
  8. stirringStirring
  9. waitis continued for approximately 30 minutes
  10. customthe solid removed by filtration
  11. washThe filter cake is thoroughly washed with water
  12. customdried at 60° -70° C.

Sources & evidence

ORD record
ord-42c09fa66af54f8598c0bcd1d47a3ccf
Source dataset
uspto-grants-1980_03
Patent number
US04191828

Reaction notes

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