Water → 1-Methoxy-2-methyl-4-nitrobenzene

HRID 1609722Notes

Reaction equation

HRID 1609722 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].F[B-](F)(F)F.[O:15]=[N+:16]=[O:17].O>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([N+:16]([O-:17])=[O:15])[CH:5]=[CH:4][C:3]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 336372-MethylanisoleHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 6435201-Methoxy-2-methyl-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methylanisole (20 g) in 500 ml dichloromethane chilled in an ice bath is treated with 27.2 g of nitronium tetrafluoroborate and stirred two days. The mixture is poured into water, the layers are separated, and the aqueous phase is washed with dichloromethane. The combined organic layers are dried, filtered, stripped, and chromatographed on silica gel with 9:1 to 8:2 hexane:ethyl acetate to give 2-methyl-4-nitroanisole. NMR (CDCl3): δ2.3 (3H,s), 3.9 (3H,s), 6.9 (1H,d), 8.0 (1H,d), 8.1 (1H,d of d).

Workup

  1. customthe layers are separated
  2. washthe aqueous phase is washed with dichloromethane
  3. customThe combined organic layers are dried
  4. filtrationfiltered
  5. customchromatographed on silica gel with 9:1 to 8:2 hexane

Sources & evidence

ORD record
ord-5f821e2a816a4074bbfd1d494b4ee69c
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

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