Hydrogen Bromide → 4(4-Chloro-3,5-dimethyl-phenoxy)-2,6-dimethyl-phenol

HRID 1155365Notes

Reaction equation

HRID 1155365 reaction equation
[Cl:1][C:2]1[C:18]([CH3:19])=[CH:17][C:5]([O:6][C:7]2[CH:12]=[C:11]([CH3:13])[C:10]([O:14]C)=[C:9]([CH3:16])[CH:8]=2)=[CH:4][C:3]=1[CH3:20].Br>C(O)(=O)C>[Cl:1][C:2]1[C:18]([CH3:19])=[CH:17][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH3:16])[C:10]([OH:14])=[C:11]([CH3:13])[CH:12]=2)=[CH:4][C:3]=1[CH3:20]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 127678104(4-Chloro-3,5-dimethyl-phenoxy)-2,6-dimethylanisole

Product 1

HCID 127678094(4-Chloro-3,5-dimethyl-phenoxy)-2,6-dimethyl-phenolYield 102.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

40 g of 4(4-chloro-3,5-dimethyl-phenoxy)-2,6-dimethylanisole were added to a solution of 125 ml of 48% hydrobromic acid and 300 ml of glacial acetic acid. The mixture was then refluxed for 2 hours at the reflux condenser. After concentration under reduced pressure, water was added to the residue and the mixture was extracted with methylene chloride. After the organic extract had been shaken several times with water, it was concentrated and the residue was distilled under greatly reduced pressure. 39 g of 4(4-chloro-3,5-dimethyl-phenoxy-2,6-dimethyl-phenol were obtained, boiling point: 186°-190° C. under a pressure of 2-3 mm mercury.

Workup

  1. temperatureThe mixture was then refluxed for 2 hours at the reflux condenser
  2. concentrationAfter concentration under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with methylene chloride
  5. extractionAfter the organic extract
  6. concentrationwas concentrated
  7. distillationthe residue was distilled under greatly reduced pressure

Sources & evidence

ORD record
ord-e9825c94285e49f78f21624c76679394
Source dataset
uspto-grants-1981_11
Patent number
US04301295

Reaction notes

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