Hydrochloric Acid → 2,4-Bis(benzyloxy)-5-bromobenzoic acid

HRID 1881371Notes

Reaction equation

HRID 1881371 reaction equation
C([O:8][C:9](=[O:33])[C:10]1[CH:15]=[C:14]([Br:16])[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][C:11]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)C1C=CC=CC=1.[OH-].[Na+].Cl>CO>[CH2:26]([O:25][C:11]1[CH:12]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]([Br:16])=[CH:15][C:10]=1[C:9]([OH:33])=[O:8])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 46915635Benzyl-2,4-bis-benzyloxy-5-bromobenzoate

Product 1

HCID 469156382,4-Bis(benzyloxy)-5-bromobenzoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask was charged with benzyl-2,4-bis-benzyloxy-5-bromobenzoate (25 g; 50 mmol); 5N aqueous sodium hydroxide (80 mL), and methanol (200 mL). The reaction was heated at reflux overnight, cooled, and acidified to pH=2 with concentrated hydrochloric acid. The solvent was reduced by half using evaporation, and the solid was filtered, washed with water (100 mL), dissolved in dichloromethane, dried with sodium sulfate, and evaporated to give 2,4-bis-benzyloxy-5-bromobenzoic acid (15.5 g; 37.5 mmol).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. customThe solvent was reduced by half using evaporation
  5. filtrationthe solid was filtered
  6. washwashed with water (100 mL)
  7. dissolutiondissolved in dichloromethane
  8. dry with materialdried with sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-915a7b1dae0647f182cb1bbc6029f7f2
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

Loading…