Sodium Hydroxide → 4-Carboxyphenylboronic Acid

HRID 378961Notes

Reaction equation

HRID 378961 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:12].[K+].[OH-:17].[Na+]>>[C:1]([C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1)([OH:12])=[O:17]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 79799Tolylboronic acidHCID 516875Potassium Permanganate

Product 1

HCID 3121834-Carboxyphenylboronic Acid

Procedure

To a solution of 4-methylphenylboronic acid (34 g, 0.25 mol) in aqueous sodium hydroxide (0.5 N, 1000 mL) was added potassium permanganate (83 g, 0.53 mol) while keeping the temperature at 35-40° C. After the addition the reaction was filtered and the filtrate acidified with concentrated hydrochloric acid (65 mL). The product was filtered off. A yield of 29.6 g was obtained. M.p. 228° C.

Workup

  1. customat 35-40° C
  2. additionAfter the addition the reaction
  3. filtrationwas filtered
  4. filtrationThe product was filtered off
  5. customA yield of 29.6 g was obtained

Sources & evidence

ORD record
ord-2115756b8fe945239a0de0ab3e2f5811
Source dataset
uspto-grants-2001_10
Patent number
US06297261B1

Reaction notes

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