Hydrogen Bromide → Phenol, 4-(4-(methylsulfonyl)phenoxy)-

HRID 2164642

Reaction equation

HRID 2164642 reaction equation
[CH3:1][S:2]([C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br>C(O)(=O)C>[CH3:1][S:2]([C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 514881Benzene, 1-methoxy-4-(4-(methylsulfonyl)phenoxy)-

Product 1

HCID 514882Phenol, 4-(4-(methylsulfonyl)phenoxy)-Yield 98.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 37.3 g of 4-(4-(methylsulfonyl)phenoxy)-1-methoxybenzene (Example 18), 41 ml of 48% aqueous hydrogen bromide and 185 ml of glacial acetic acid was heated at reflux under nitrogen for 21 hrs. The reaction mixture was cooled and the solvent removed in vacuo. The product was collected by filtration, washed well with water and dried, which gave 35.0 g (98.9% yield) of the product. Recrystallization from aqueous ethanol gave purified 4-(4-(methylsulfonyl)phenoxy)phenol, mp 129°-130° C.

Workup

  1. temperatureat reflux under nitrogen for 21 hrs
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed in vacuo
  4. filtrationThe product was collected by filtration
  5. washwashed well with water
  6. customdried

Sources & evidence

ORD record
ord-76d78786cedf40808e47d51e708b1537
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Linked notes

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