Water → 1,3-Bis(4-hydroxyphenoxy)benzene

HRID 30955Notes

Reaction equation

HRID 30955 reaction equation
C[O:2][C:3]1[CH:24]=[CH:23][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=3)[CH:9]=2)=[CH:5][CH:4]=1.O>Br.C(O)(=O)C>[C:10]1([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:11]=[CH:12][CH:13]=[C:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:24][CH:23]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 962WaterHCID 6295191,3-Bis(4-methoxyphenoxy)benzene

Product 1

HCID 6263111,3-Bis(4-hydroxyphenoxy)benzeneYield 102.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent2×

Procedure

22 g of the above-described compound from Example 20 are dissolved, under argon, in a mixture of 60 ml of hydrobromic acid (48% solution) and 150 ml of hydrogen bromide in glacial acetic acid (33% solution), and the mixture is heated, adjusted to the evolution of gas, at reflux. After a total of 5 hours, 300 ml of water are added dropwise, with cooling. The batch is extracted several times with a total of 400 ml of diethyl ether. The combined organic phases are washed four times using 400 ml of water each time, dried over magnesium sulfate and filtered. The solvent is removed in vacuo. 20.5 g of a crystalline solid are obtained, which was purified over a column with silica gel (0.063-0.20 mm) (eluant: n-hexane/ethyl acetate 3:1). The solvent is removed and the product is dried in vacuo. 15.8 g of a beige solid are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux
  3. temperaturewith cooling
  4. extractionThe batch is extracted several times with a total of 400 ml of diethyl ether
  5. washThe combined organic phases are washed four times
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7db6aea1634f4dd29af4a52244376014
Source dataset
uspto-grants-2008_09
Patent number
US07425358B2

Reaction notes

Loading…