Sodium Hydroxide → 3-Carboxyphenylboronic acid

HRID 2081158Notes

Reaction equation

HRID 2081158 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([B:7]([OH:9])[OH:8])[CH:2]=1.[Mn]([O-])(=O)(=O)=[O:12].[K+].[OH-:17].[Na+]>>[C:10]([C:1]1[CH:2]=[C:3]([B:7]([OH:9])[OH:8])[CH:4]=[CH:5][CH:6]=1)([OH:12])=[O:17]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 27339503-Tolylboronic acid

Product 1

HCID 27339573-Carboxyphenylboronic acid

Procedure

To a solution of m-Tolylboronic acid (8.0 g, 0.059 mol) in 10% sodium hydroxide (250 ml) was added potassium permanganate (20 g) in small portions. The reaction mixture was stirred at room temperature for 48 hours. The precipitated manganese dioxide was filtered and the filtrate was acidified with 10% sulfuric acid and cooled. The white precipitate that formed was filtered and recrystallized from water. M.P. 250°-52° C.

Workup

  1. filtrationThe precipitated manganese dioxide was filtered
  2. temperaturecooled
  3. customThe white precipitate that formed
  4. filtrationwas filtered
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-d2df728ca8bf42e3a0b97f24ee050516
Source dataset
uspto-grants-1993_02
Patent number
US05183653

Reaction notes

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