Sodium Hydroxide → 3-(Benzyloxy)-4-bromo-5-methoxybenzoic acid

HRID 579304Notes

Reaction equation

HRID 579304 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:20][CH3:21])[C:18]=1[Br:19])[C:12]([O:14]C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:20][CH3:21])[C:18]=1[Br:19])[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86710604Methyl 3-(benzyloxy)-4-bromo-5-methoxybenzoate

Product 1

HCID 867106053-(Benzyloxy)-4-bromo-5-methoxybenzoic acidYield 95.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(benzyloxy)-4-bromo-5-methoxybenzoate (3.72 g, 10.59 mmol) in 1:1 MeOH/THF (50 mL) was added aqueous sodium hydroxide (1 M, 53.0 mL, 53.0 mmol). After 10 minutes the volatiles were removed under reduced pressure and the solution acidified to pH 1 by addition of concentrated hydrochloric acid resulting in formation of a thick white precipitate. The mixture was extracted with ethyl acetate (2×), and DCM (3×). The combined extracts were washed with brine, dried over magnesium sulfate and concentrated to provide 3-(benzyloxy)-4-bromo-5-methoxybenzoic acid as a white solid (3.41 g). MS (M−1)=335.0. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.21-7.49 (m, 7H), 5.16 (s, 2H), 3.91 (s, 3H).

Workup

  1. customAfter 10 minutes the volatiles were removed under reduced pressure
  2. additionthe solution acidified to pH 1 by addition of concentrated hydrochloric acid resulting in formation of a thick white precipitate
  3. extractionThe mixture was extracted with ethyl acetate (2×), and DCM (3×)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-536684a44b75468ca5bbbac04a8a5fdd
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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