Acetonitrile → 3-Hydroxy3, 3-di(4-biphenylyl) propionitrile

HRID 1110493Notes

Reaction equation

HRID 1110493 reaction equation
[C:1]1([C:7]2[CH:26]=[CH:25][C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27](#[N:29])[CH3:28].[NH2-].[Na+]>C1C=CC=CC=1>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:26]=[CH:25][C:10]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)([OH:12])[CH2:28][C:27]#[N:29])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24533Sodium amideHCID 2284534,4'-Diphenylbenzophenone

Product 1

HCID 221552003-Hydroxy3, 3-di(4-biphenylyl) propionitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred suspension of 4,4'-diphenylbenzophenone (15.5 g) and acetonitrile in dry benzene (200 mL), was added at a rapid dropwise rate a suspension of sodamide (2.3 g) in dry benzene (20 mL). The resulting mixture was stirred at reflux for 60 minutes, then the reaction was cooled and treated carefully with ice (50 g). The layers were separated, and the aqueous Phase was extracted with toluene. The organic extracts were washed with water, then were combined, dried (MgSO4) and evaporated to furnish 13.5 g of 3,3-bis[(1,1'-biphenyl)-4-yl]-3-hydroxypropanenitrile as an oil. The material was contained a minor impurity that was presumed to be the starting ketone.

Workup

  1. additionwas added at a rapid dropwise rate
  2. temperatureat reflux for 60 minutes
  3. temperaturethe reaction was cooled
  4. customThe layers were separated
  5. extractionthe aqueous Phase was extracted with toluene
  6. washThe organic extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-0be86b7d7b724bf6b1914e0ffd4ba9fe
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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