HCID 54448051, compound → HCID 22915050, compound

HRID 234225Notes

Reaction equation

HRID 234225 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[C:9]([CH3:10])=[C:8]([OH:11])[CH:7]=[C:6]([O:12][CH3:13])[C:5]=1[Br:14]>[OH-].[Na+]>[Br:14][C:5]1[C:6]([O:12][CH3:13])=[CH:7][C:8]([OH:11])=[C:9]([CH3:10])[C:4]=1[C:3]([OH:15])=[O:2]

Participants

3

Reactant 1

HCID 54448051HCID 54448051, compound

Product 1

HCID 22915050HCID 22915050, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 23 g 2-bromo-5-hydroxy-3-methoxy-6-methylbenzoic acid methyl ester in 200 ml of 3N sodium hydroxide was stirred at 70° C. for 85 h. The cooled solution was washed with diethyl ether and then acidified to pH 1 by the addition of 3N hydrochloric acid. The aqueous layer was extracted with diethyl ether and the organic phase was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was recrystallized from diethyl ether/pentane to yield 21 g of 2-bromo-5-hydroxy-3-methoxy-6-methyl-benzoic acid as white crystals, m.p.79°-80° C.

Workup

  1. washThe cooled solution was washed with diethyl ether
  2. additionacidified to pH 1 by the addition of 3N hydrochloric acid
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. washthe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from diethyl ether/pentane

Sources & evidence

ORD record
ord-f55f156cfa9643dd91ec5fd5e6ef7a5a
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

Loading…