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

HRID 334827Notes

Reaction equation

HRID 334827 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].[ClH:20]>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[N:1]1[N:2]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH2:11][Cl:20])[C:18]=2[OH:19])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 17113Drometrizole

Product 1

HCID 547519482-(2H-Benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

2-(2H-Benzotriazol-2-yl)-4-methyl-phenol (2.3 g, 10 mmol) is dissolved in acetic acid (30 mL) at 80° C. Zinc chloride (140 mg, 1 mmol) and paraformaldehyde (390 mg, 13 mmol) are added and HCl gas is passed through the reaction mixture for 12 hours at 80° C. The product, which precipitates after cooling to room temperature, is filtered off, washed with small amounts of cold ethyl acetate and dried at 60° C. under vacuum to yield 1.9 g of 2-(2H-benzotriazol-2-yl)-6-chloromethyl-4-methyl-phenol.

Workup

  1. customThe product, which precipitates
  2. filtrationis filtered off
  3. washwashed with small amounts of cold ethyl acetate
  4. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-f9c7c5bc930e4475bfbfef919f2a9698
Source dataset
uspto-grants-2014_11
Patent number
US08883829B2

Reaction notes

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