Toluene → 4-(2,2-Diphenylethoxy)-pyridine-1-oxide

HRID 1680078Notes

Reaction equation

HRID 1680078 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[N+]([C:21]1[CH:26]=[CH:25][N+:24]([O-:27])=[CH:23][CH:22]=1)([O-])=O.C1(C)C=CC=CC=1>CN(C)C=O>[C:10]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][O:9][C:21]2[CH:26]=[CH:25][N+:24]([O-:27])=[CH:23][CH:22]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 143004-Nitropyridine N-oxideHCID 24758Sodium hydrideHCID 74662beta-Phenylphenethyl alcohol

Product 1

HCID 234590834-(2,2-Diphenylethoxy)-pyridine-1-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2,2-diphenylethanol (4 g, 0.02 m) was added portionwise to a suspension of sodium hydride (0.48 g, 0.02 m) in dry dimethylformamide (200 ml) under nitrogen. After the reaction had ceased, the mixture was added dropwise to a solution of 4-nitropyridine-1-oxide (2.8 g, 0.02 m) in dry dimethylformamide (100 ml) at 35°-40° C. The mixture was maintained at this temperature for 12 hours and then filtered. The solvent was removed under reduced pressure, leaving a residue that was heated with successive portions of toluene. The toluene solution was evaporated to an oil which was crystallised from a mixture of toluene and 60-80 petrol (1:1). This gave 4-(2,2-diphenylethoxy)pyridine-1-oxide (2.2 g) as orange crystals, m.pt. 134°-138° C.

Workup

  1. temperatureThe mixture was maintained at this temperature for 12 hours
  2. filtrationfiltered
  3. customThe solvent was removed under reduced pressure
  4. customleaving a residue that
  5. customThe toluene solution was evaporated to an oil which
  6. customwas crystallised from a mixture of toluene and 60-80 petrol (1:1)

Sources & evidence

ORD record
ord-cd565dc1e91547d1b1f23ce49467e840
Source dataset
uspto-grants-1981_06
Patent number
US04271304

Reaction notes

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