Propiolic Acid → 1-Benzyl-1H-1,2,3-triazole-4-carboxylic acid
Reaction equation
[CH2:1]([N:8]=[N+:9]=[N-:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([OH:15])(=[O:14])[C:12]#[CH:13]>CC(C)=O>[CH2:1]([N:8]1[CH:13]=[C:12]([C:11]([OH:15])=[O:14])[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 84 milliliters (ml) of acetone and 35.8 grams (g) (269 mmoles) of benzyl azide, 19.3 g (276 mmoles) of propiolic acid was added by drop. The reaction mixture was stirred and heated to reflux overnight. After cooling to 0° C., 33.6 g (62%) of 1(2 or 3)-benzyl-1H-1,2,3-triazole-4-carboxylic acid precipitated from the reaction solution as white crystals. The structure was confirmed by nuclear magnetic resonance (n.m.r.) and infrared spectroscopy (I.R.).