Potassium Hydroxide → 3-Bromo-4-methoxyphenol

HRID 2097589Notes

Reaction equation

HRID 2097589 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]([O:12]C(=O)C)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]>O.CO>[Br:3][C:4]1[CH:5]=[C:6]([OH:12])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 145058743-Bromo-4-methoxyphenyl acetate

Product 1

HCID 6088153-Bromo-4-methoxyphenolYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (290 mg, 5.19 mmol) in water (2.5 mL) was added to a solution of acetic acid 3-bromo-4-methoxy-phenyl ester (1.2 g, 4.9 mmol) in methanol (18.5 mL). Mixture was stirred at ambient temperature for 30 min, then solvents were removed in vacuo and water (40 mL) added. The mixture was made acidic by drop-wise addition of 1.2 M aq HCl solution (4.3 mL) and the mixture extracted with dichloromethane (2×40 mL). Combined organics were dried over sodium sulphate, filtered and filtrate solvents evaporated in vacuo to give the title compound (976 mg, 98%) as a pale yellow solid.

Workup

  1. customsolvents were removed in vacuo and water (40 mL)
  2. additionadded
  3. additionThe mixture was made acidic by drop-wise addition of 1.2 M aq HCl solution (4.3 mL)
  4. extractionthe mixture extracted with dichloromethane (2×40 mL)
  5. dry with materialCombined organics were dried over sodium sulphate
  6. filtrationfiltered
  7. customfiltrate solvents evaporated in vacuo

Sources & evidence

ORD record
ord-cb11fefe9fa3490cb62d5b568c6c1ffd
Source dataset
uspto-grants-2013_05
Patent number
US08450346B2

Reaction notes

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