Ethanol → 3-Carboxyphenylboronic acid

HRID 1837952Notes

Reaction equation

HRID 1837952 reaction equation
[O-][Mn](=O)(=O)=O.[K+].[CH3:7][C:8]1[CH:9]=[C:10]([B:14]([OH:16])[OH:15])[CH:11]=CC=1.[OH-:17].[Na+].[CH3:19][CH2:20][OH:21]>O>[C:20]([C:19]1[CH:11]=[C:10]([B:14]([OH:16])[OH:15])[CH:9]=[CH:8][CH:7]=1)([OH:17])=[O:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 27339503-Tolylboronic acid

Product 1

HCID 27339573-Carboxyphenylboronic acidYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
55 °C

Procedure

A solution of KMnO4 (3.7 g, 23.4 mmol) in water (100 mL) was slowly added to a solution of (3-methylphenyl)boronic acid (1.5 g, 11 mmol) and NaOH (1 g, 25 mmol) in water (60 mL), while the temperature was maintained between 30° C. and 40° C. using a water bath. The resulting brown suspension was heated at 55° C. for 2 h and allowed to cool to room temperature. EtOH (1 mL) was added, the resulting slurry was filtered and the filtrate concentrated to 100 mL under reduced pressure. The resulting mixture was acidified with conc. HCl (1.5 mL) and kept at 5° C. overnight. The white suspension was filtered to give (3-carboxyphenyl)boronic acid (1.44 g, 79%) as a white solid: 1H NMR (D2O) δ 7.51 (m, 1H), 7.99 (m, 1H), 8.07 (m, 1H), 8.4 (s, 1H).

Workup

  1. temperaturewas maintained between 30° C. and 40° C.
  2. temperatureto cool to room temperature
  3. filtrationthe resulting slurry was filtered
  4. concentrationthe filtrate concentrated to 100 mL under reduced pressure
  5. filtrationThe white suspension was filtered

Sources & evidence

ORD record
ord-b070b3b0cbb14e74bd932a743174fdf2
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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