Sodium Hydroxide → 2-Hydroxydiphenyl ether

HRID 1078049Notes

Reaction equation

HRID 1078049 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>ClCCCl.ClC(Cl)C>[O:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2487582-Methoxyphenyl phenyl ether

Product 1

HCID 754912-Hydroxydiphenyl etherYield 82.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 23.4 g (74.9 mmol) of boron tribromide-dimethyl sulfide complex in 150 mL of 1,2-dichloroethane was added dropwise to 3.00 g (15.0 mmol) of 2-methoxyphenyl phenyl ether in 50 mL dichloroethane at room temperature. The mixture was stirred at reflux overnight. 50 mL 3M NaOH was added to quench the reaction. After separation of layers, the organic layer was extracted with 3×100 mL 3M NaOH. The combined aqueous layer was acidified with conc. HCl, and the precipitated product was extracted with 3×150 mL ethyl ether. After washing with brine solution, drying over MgSO4, and filtering, solvents were evaporated under reduced pressure to give 2.30 g (82.4%) of an off-white solid, which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 5.57 (s, 1H); 6.81-6.90 (m, 2H); 7.01-7.07 (m, 4H); 7.12 (t, 1H, J=7.3 Hz); 7.31-7.38 (m, 2H). ##STR105##

Workup

  1. temperatureat reflux overnight
  2. customto quench
  3. customthe reaction
  4. customAfter separation of layers
  5. extractionthe organic layer was extracted with 3×100 mL 3M NaOH
  6. extractionthe precipitated product was extracted with 3×150 mL ethyl ether
  7. washAfter washing with brine solution
  8. dry with materialdrying over MgSO4
  9. filtrationfiltering
  10. customsolvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-f93c44c2968c4b3d9537d3a191ec11f0
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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