Hydrogen Bromide → 4-(3-Methylphenoxy)phenol

HRID 1732162Notes

Reaction equation

HRID 1732162 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)[CH:2]=1.Br>C(O)(=O)C>[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 347990NSC406958

Product 1

HCID 155619644-(3-Methylphenoxy)phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

77 g of p-(m-tolyloxy)anisole are dissolved in 360 ml of acetic acid and treated with 300 ml of 48% hydrobromic acid. Then the mixture is allowed to react at reflux temperature for 5 hours. The cooled solution is poured into 1.5 l of ice/water and extracted three times with 150 ml of methylene chloride each time. The organic solution is washed three times with 150 ml of water each time and with 150 ml of saturated sodium bicarbonate solution, dried over anhyrous sodium sulfate and evaporated. Distillation of the crude product yields pure p-(m-tolyloxy)phenol; b.p. 88°-89° C./0.04 Torr.

Workup

  1. customto react
  2. temperatureat reflux temperature for 5 hours
  3. extractionextracted three times with 150 ml of methylene chloride each time
  4. washThe organic solution is washed three times with 150 ml of water each time
  5. dry with materialwith 150 ml of saturated sodium bicarbonate solution, dried over anhyrous sodium sulfate
  6. customevaporated
  7. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-b556730702f14d8ba94b0235853888b4
Source dataset
uspto-grants-1986_11
Patent number
US04625048

Reaction notes

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