Sodium Hydroxide → 5-Bromo-2-methoxyphenol

HRID 1940333Notes

Reaction equation

HRID 1940333 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-66d0f59032b1424799e6360b87fc20aa
Source dataset
uspto-grants-1997_12
Patent number
US05698711

Reaction notes

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