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

HRID 1359159Notes

Reaction equation

HRID 1359159 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-de3e99eaae8149a1803eb13a6fe40330
Source dataset
uspto-grants-2003_07
Patent number
US06599942B1

Reaction notes

Loading…