Acetic Acid → 2-Methyl-4-nitrophenol

HRID 1609723Notes

Reaction equation

HRID 1609723 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11]C.Br.C(O)(=O)C>O>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 6435201-Methoxy-2-methyl-4-nitrobenzene

Product 1

HCID 74422-Methyl-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Methyl-4-nitroanisole (4.0 g) in 50 ml 1:1 hydrobromic acid:acetic acid is heated 12 hours at 120°. Solvent is stripped, the residue taken up in water and ethyl acetate, the mixture is filtered to remove insolubles, and the layers are separated. The organic phase is dried, filtered, and stripped to afford 2-methyl-4-nitrophenol. NMR (CDCl3): δ2.3 (3H,s), 6.8 (1H,d), 7.9 (1H,d of d), 8.0 (1H,d).

Workup

  1. filtrationethyl acetate, the mixture is filtered
  2. customto remove insolubles
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered

Sources & evidence

ORD record
ord-477934147fb64af681897afe9126db83
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

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