Hydrochloric Acid → 2-(3-Bromophenyl)-2-hydroxypropanoic acid

HRID 886589Notes

Reaction equation

HRID 886589 reaction equation
C([O:3][C:4](=[O:15])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1)([OH:7])[CH3:6])C.[OH-].[K+].Cl>CO>[Br:14][C:10]1[CH:9]=[C:8]([C:5]([OH:7])([CH3:6])[C:4]([OH:15])=[O:3])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59824992HCID 59824992, compound

Product 1

HCID 598250602-(3-Bromophenyl)-2-hydroxypropanoic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(3-Bromo-phenyl)-2-hydroxy-propionic acid ethyl ester (1.87 g, 6.7 mmol) in methanol (10 mL) was added potassium hydroxide (50% in water, 2 mL) and the solution was stirred at room temperature for 15 minutes. Hydrochloric acid (1 N) was added to adjust the pH to 4. The resulting mixture was extracted with ethyl acetate (10 ml×3). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford the crude 2-(3-bromo-phenyl)-2-hydroxy-propionic acid as a white solid (1.6 g, 97%). MS: m/z 245 (M+H+).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (10 ml×3)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5948dabbdce04dd2af46a5e89f622a8d
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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