Water → 2-Hydroxydiphenyl ether

HRID 358265Notes

Reaction equation

HRID 358265 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I.C(OC(=O)C)(=O)C.O>CCOCC.C(O)(=O)C>[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 24841Hydrogen iodideHCID 2487582-Methoxyphenyl phenyl ether

Product 1

HCID 754912-Hydroxydiphenyl etherYield 83.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10 g of o-phenoxyanisol, 80 ml of hydroiodic acid (52%), 80 ml of acetic acid and 40 ml of acetic anhydride was refluxed for 1.5 hours. After being cooled, the reaction mixture was poured into ice-water to deposit a precipitate. The precipitate was dissolved in ether, and the solution was washed with an aqueous saturated sodium chloride solution, an aqueous saturated thiosulfuric acid aqueous solution and then an aqueous saturated sodium chloride solution. This ether solution was dried over anhydrous sodium sulfate, and the solvent was removed to give yellow solids. The solids were dissolved in acetic acid and stirred. The mixture was poured into cold water to deposit crystals. The crystals were washed with water and then with n-hexane, and dried at 80° C. under reduced pressure to obtain 7.8 g of o-phenoxyphenol as slightly yellow powders.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperatureAfter being cooled
  3. washthe solution was washed with an aqueous saturated sodium chloride solution
  4. dry with materialThis ether solution was dried over anhydrous sodium sulfate
  5. customthe solvent was removed
  6. customto give yellow solids
  7. washThe crystals were washed with water
  8. dry with materialwith n-hexane, and dried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-210b72ce6c7d44fd90a6799f26cc4adf
Source dataset
uspto-grants-1984_08
Patent number
US04465851

Reaction notes

Loading…