Acetic Acid → 4-(2,6-Dimethyl-4-nitrophenoxy)phenol

HRID 2120298Notes

Reaction equation

HRID 2120298 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=1.C(O)(=O)C.Br>O>[CH3:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 100846724-(4-Methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

Product 1

HCID 140285904-(2,6-Dimethyl-4-nitrophenoxy)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of the title A compound, 3,5-dimethyl-4-(4′-methoxyphenoxy)nitrobenzene (16.4 g, 60 mmol), acetic acid (AcOH; 100 mL) and aqueous 48% hydrobromic acid (HBr; 100 mL) is heated at 120° C. for 16 h. The mixture is cooled to RT, diluted with water (200 mL) and the precipitated product is collected by vacuum filtration, washed with water and hexanes and dried in vacuo to afford 3,5-dimethyl-4-(4′-hydroxyphenoxy)nitrobenzene: NMR (CDCl3) 2.22 (s, 6H), 6.62 (d, 2H, J=8.7), 6.77 (d, 2H, J=8.7), 8.0 (s, 2H).

Workup

  1. temperatureThe mixture is cooled to RT
  2. filtrationthe precipitated product is collected by vacuum filtration
  3. washwashed with water and hexanes
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d459f55c36564a96b43c2890e71bf525
Source dataset
uspto-grants-2004_02
Patent number
US06689896B2

Reaction notes

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