Sodium Hydroxide → 5-Bromo-2-methoxyphenol

HRID 1489734Notes

Reaction equation

HRID 1489734 reaction equation
C([O:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])(=O)C1C=CC=CC=1.[OH-].[Na+]>O.C(O)C>[Br:16][C:14]1[CH:13]=[CH:12][C:11]([O:17][CH3:18])=[C:10]([OH:9])[CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21187844HCID 21187844, compound

Product 1

HCID 1422285-Bromo-2-methoxyphenolYield 98.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-benzoyloxy-4-bromoanisole (5 g) and sodium hydroxide (3 g) in water (5 mL) and ethanol (50 mL) is heated at reflux for 1 hour 30 minutes. It is then evaporated and the residue is triturated with water (20 mL) and concentrated hydrochloric acid (10 mL) and extracted with dichloromethane (150 mL). The organic solution is washed with saturated aqueous sodium bicarbonate solution (3×25 mL), dried, and concentrated, to give 5-bromo-2-methoxyphenol (3.25 g), in the form of a white crystalline solid, m.p. 67°-68° C.

Workup

  1. temperatureat reflux for 1 hour 30 minutes
  2. customIt is then evaporated
  3. customthe residue is triturated with water (20 mL) and concentrated hydrochloric acid (10 mL)
  4. extractionextracted with dichloromethane (150 mL)
  5. washThe organic solution is washed with saturated aqueous sodium bicarbonate solution (3×25 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d1da383821f143ada55a7d1602f6a010
Source dataset
uspto-grants-1997_10
Patent number
US05679696

Reaction notes

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