Benzhydrol → HCID 23459080, compound

HRID 1680076Notes

Reaction equation

HRID 1680076 reaction equation
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[N+]([C:20]1[CH:25]=[CH:24][N+:23]([O-:26])=[CH:22][CH:21]=1)([O-])=O>CN(C)C=O>[C:9]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][C:20]2[CH:25]=[CH:24][N+:23]([O-:26])=[CH:22][CH:21]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7037BenzhydrolHCID 143004-Nitropyridine N-oxideHCID 24758Sodium hydride

Product 1

HCID 23459080HCID 23459080, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Diphenylmethanol (18.4 g, 0.1 m) was added portionwise to a suspension of sodium hydride (2.4 g, 0.1 m) in dimethylformamide (300 ml) under nitrogen. After the reaction had ceased, the suspension was treated dropwise with a solution of 4-nitropyridine-1-oxide (14 g, 0.1 m) in dimethylformamide (500 ml). This caused the colour of the mixture to change from orange to dark blue. After a further twelve hours at room temperature, the mixture was filtered and evaporated under reduced pressure, leaving a residue that crystallised from toluene giving 19.8 g of 4-[diphenylmethoxy]pyridine-1-oxide as light yellow crystals, m.pt. 155°-157° C.

Workup

  1. waitAfter a further twelve hours at room temperature
  2. filtrationthe mixture was filtered
  3. customevaporated under reduced pressure
  4. customleaving a residue
  5. customthat crystallised from toluene giving 19.8 g of 4-[diphenylmethoxy]pyridine-1-oxide as light yellow crystals, m.pt. 155°-157° C.

Sources & evidence

ORD record
ord-f5e418eb12884a638685bc173d287fb1
Source dataset
uspto-grants-1981_06
Patent number
US04271304

Reaction notes

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