Acetic Acid → 2-Methyl-4-nitrophenol

HRID 2256487Notes

Reaction equation

HRID 2256487 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): δ 2.3 (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-ec91f4ce3e084e2382186a1e7d0f9833
Source dataset
uspto-grants-1997_08
Patent number
US05654468

Reaction notes

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