Sodium Hydroxide → 4-Bromo-3,5-diethoxybenzoic acid

HRID 38480Notes

Reaction equation

HRID 38480 reaction equation
[Br:1][C:2]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[O:15][CH2:16][CH3:17].[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57930905Methyl 4-bromo-3,5-diethoxybenzoate

Product 1

HCID 579309874-Bromo-3,5-diethoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-bromo-3,5-diethoxybenzoate (3.00 g) in a mixture of THF (25 ml) and MeOH (10 ml) was added aqueous 1N NaOH (20 ml) and the reaction mixture was stirred at room temperature for 6 h. The mixture was concentrated under reduced pressure and the residue was diluted with H2O and diethylether. The aqueous layer was acidified with aqueous 1N HCl, the mixture was extracted with CHCl3 and dried over sodium sulfate. After filtration and concentration, the residue was dried in vacuo to give the crude intended compound as a colorless solid. Thus obtained crude product was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with H2O and diethylether
  3. extractionthe mixture was extracted with CHCl3
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe residue was dried in vacuo
  7. customto give the crude
  8. customThus obtained crude product
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-a47a94cc5a9e4777ab1d821f29080afe
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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