Hydrochloric Acid → 2-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol

HRID 341257Notes

Reaction equation

HRID 341257 reaction equation
[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2O)[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH2:18]=[O:19].S(=O)(=O)(O)O.[ClH:25]>C(O)(=O)C>[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH2:11][Cl:25])[C:18]=2[OH:19])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 17113Drometrizole

Product 1

HCID 547519482-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenolYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(2H-benzotriazol-2-yl)-4-methyl-phenol (100.0 g, 0.44 mol), paraformaldehyde (26.4 g, 0.88 mol), sulphuric acid (10.9 g, 110 mmol), conc. HCl (200 mL), and acetic acid (500 mL) is heated to 90° C. for six hours. The precipitated product is isolated by filtration and washed subsequently with AcOH, AcOH:heptane (1:1), and heptane and dried at 45° C. (95% yield).

Workup

  1. customThe precipitated product is isolated by filtration
  2. washwashed subsequently with AcOH, AcOH:heptane (1:1), and heptane
  3. customdried at 45° C. (95% yield)

Sources & evidence

ORD record
ord-8bc348d0939c466f93dacaaeffa756d6
Source dataset
uspto-grants-2014_11
Patent number
US08895754B2

Reaction notes

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