Formaldehyde → 1H-Benzotriazole-1-methanol

HRID 1703047Notes

Reaction equation

HRID 1703047 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.C=O.[OH-].[Na+].[C:14](OCC)(=[O:16])C>CN(C)C=O>[OH:16][CH2:14][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178418385HCID 178418385, compound

Product 1

HCID 2241691H-Benzotriazole-1-methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of benzotriazole (11.9 g) and 30% formalin (8.3 ml) was heated to reflux in 100 ml of 25% aqueous dimethylformamide. A trace of starting material remained. The solution was treated with 1.0 ml of 10% aqueous sodium hydroxide and heated to reflux again. An aqueous ethyl acetate extractive work up afforded 1-(hydroxymethyl)benzotriazole (8.65 g).

Workup

  1. temperatureheated
  2. temperatureto reflux again

Sources & evidence

ORD record
ord-d3c2af53391b491794bf18de849f3f96
Source dataset
uspto-grants-1982_09
Patent number
US04350752

Reaction notes

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