1,3-Propanediol → 4-(1,3,2-Dioxaborolan-2-yl)benzoic acid

HRID 1785805Notes

Reaction equation

HRID 1785805 reaction equation
[OH:1][B:2]([OH:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH2:13](O)[CH2:14]CO>C1(C)C=CC=CC=1>[O:1]1[CH2:14][CH2:13][O:12][B:2]1[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 104421,3-PropanediolHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 223918264-(1,3,2-Dioxaborolan-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(dihydroxyboryl)benzoic acid (30.00 g, 181 mmol) and 1,3-propanediol (15.20 g, 200 mmol) in toluene (750 mL) at 140° C. was stirred for 6 hours while collecting the water removed by azeotrope formation. The mixture was concentrated to provide the desired product.

Workup

  1. customwhile collecting the water
  2. customremoved by azeotrope formation
  3. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-e7a8d8b07c8d499dbe60f2182eb14108
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

Loading…