Benzoic Acid → 1-(Benzoyloxy)-1H-1,2,3-benzotriazole

HRID 1733672Notes

Reaction equation

HRID 1733672 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O[N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1)(=O)=O>C(N(CC)CC)C.ClCCl>[C:1]([O:9][N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 243Benzoic AcidHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 5552441-(Benzoyloxy)-1H-1,2,3-benzotriazoleYield 104.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Benzoic acid (2.44 g) is dissolved in a solution of triethylamine (2.80 ml) in dichloromethane (20 ml) under ice-cooling. To the solution is added 1-methanesulfonyloxy-1,2,3-benzotriazole (4.26 g) and the mixture is stirred at room temperature for 3 hours. The reaction mixture is washed with water, a saturated aqueous sodium hydrogen carbonate and water in order and dried to give crystals of 1-benzoyloxy-1,2,3-benzotriazole (5.0 g). The product is dissolved in dichloromethane (20 ml) and thereto are added triethylamine (2.80 ml) and methanol (4.8 ml) and the mixture is stirred at room temperature for 1 hour. The reaction mixture is washed with water, an aqueous sodium hydrogen carbonate and water in order, dried and then the solvent is distilled off to give methyl benzoate (2.39 g). Infrared spectrum: 1728 cm-1.

Workup

  1. temperaturecooling
  2. washThe reaction mixture is washed with water
  3. dry with materiala saturated aqueous sodium hydrogen carbonate and water in order and dried

Sources & evidence

ORD record
ord-bf257936d358466cace1759fab3f810e
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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