Water → 4-Formylphenylboronic acid pinacol ester

HRID 1369184Notes

Reaction equation

HRID 1369184 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1)=[O:2].O[C:13]([C:16](O)([CH3:18])[CH3:17])([CH3:15])[CH3:14].O>C1(C)C=CC=CC=1>[CH3:14][C:13]1([CH3:15])[C:16]([CH3:18])([CH3:17])[O:11][B:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:8][CH:7]=2)[O:10]1

Participants

5

Reactant 3

HCID 962Water2×HCID 6425PinacolHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 27695364-Formylphenylboronic acid pinacol esterYield 93.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 5 g (33.3 mmol) of 4-formylphenylboronic acid and 3.93 g (33.3 mmol) of pinacol in 25 ml of toluene was refluxed on a water separator. When all the water of reaction had been removed, a clarifying filtration was carried out, and the solvent was removed by distillation until the product started to crystallize, giving 7.2 g (31 mmol) of product.

Workup

  1. customhad been removed
  2. filtrationa clarifying filtration
  3. customthe solvent was removed by distillation until the product
  4. customto crystallize

Sources & evidence

ORD record
ord-420657fc949e4342a9fd07868d106961
Source dataset
uspto-grants-2003_06
Patent number
US06576789B1

Reaction notes

Loading…