Nitric Acid → 3-(Dihydroxyboranyl)-5-nitrobenzoic acid

HRID 2081159Notes

Reaction equation

HRID 2081159 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([B:10]([OH:12])[OH:11])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[N+:13]([C:8]1[CH:7]=[C:6]([B:10]([OH:12])[OH:11])[CH:5]=[C:4]([C:1]([OH:3])=[O:2])[CH:9]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27339573-Carboxyphenylboronic acid

Product 1

HCID 27733153-(Dihydroxyboranyl)-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred slurry of m-carboxyphenylboronic acid (5 g, 0.03 mol) in concentrated sulfuric acid (15 ml) was added fuming nitric acid (15 ml, d=1.54). The reaction mixture was stirred at room temperature for 45 minutes and poured on ice (150 g). The nitro acid formed was filtered, washed with water and dried. M.P. 235°-37° C.

Workup

  1. additionpoured on ice (150 g)

Sources & evidence

ORD record
ord-078ab87e04cb4982b30680c858fc62c4
Source dataset
uspto-grants-1993_02
Patent number
US05183653

Reaction notes

Loading…