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

HRID 2356076Notes

Reaction equation

HRID 2356076 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][CH2:15]O>C1(C)C=CC=CC=1>[O:1]1[CH2:15][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 145278654-(1,3,2-Dioxaborinan-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-8a80a9a9a3624b2cac0e71a14c74c267
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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