4-Hydroxy-3-methylbenzonitrile → HCID 67141374, compound

HRID 400593Notes

Reaction equation

HRID 400593 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].F[B-](F)(F)F.[O:16]=[N+:17]=[O:18]>C(#N)C.O>[OH:1][C:2]1[C:9]([N+:17]([O-:18])=[O:16])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 2

HCID 109645604-Hydroxy-3-methylbenzonitrileHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 67141374HCID 67141374, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 4-hydroxy-3-methylbenzonitrile (3.1 g, 23.3 mmol) in 60 mL of anhydrous acetonitrile was cooled to −30° C. and treated with nitronium tetrafluoroborate (3.4 g, 25.6 mmol) in portions. After 60 minutes, the reaction mixture was diluted with 100 mL of water. The resulting light yellow precipitate was filtered, washed with water, and dried to give 3.9 g of 4-hydroxy-3-methyl-5-nitrobenzonitrile (94% yield).

Workup

  1. filtrationThe resulting light yellow precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-9bd1239af7614a7b8aafa67a12e09874
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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