Toluene → 2-(5-Chloro-2H-benzotriazol-2-yl)-4-methyl-phenol

HRID 334836

Reaction equation

HRID 334836 reaction equation
C([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([N:12]2[N:16]=[C:15]3[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:14]3=[N:13]2)[C:6]=1[OH:22])(C)(C)C.C1(C)C=CC=CC=1>>[Cl:21][C:19]1[CH:18]=[CH:17][C:15]2=[N:16][N:12]([C:7]3[CH:8]=[C:9]([CH3:11])[CH:10]=[CH:5][C:6]=3[OH:22])[N:13]=[C:14]2[CH:20]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 62531Tinuvin

Product 1

HCID 131302032-(5-Chloro-2H-benzotriazol-2-yl)-4-methyl-phenolYield 85.1%

Procedure

To a solution of 2-tert-Butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methyl-phenol (50.0 g, 158 mmol) in toluene (700 ml) aluminium trichloride (42.2 g, 317 mmol) is added at 80° C. and the reaction mixture is stirred for 30 minutes, cooled to room temperature and slowly poured on crushed ice. The aqueous phase is extracted with ethyl acetate. The organic layer is washed with water, dried over sodium sulphate, filtered and evaporated to dryness. The crude product is purified by column chromatography (ethyl acetate/heptane 1:12) to yield 34.9 g of 2-(5-Chloro-2H-benzotriazol-2-yl)-4-methyl-phenol.

Workup

  1. additionslowly poured
  2. customon crushed ice
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product is purified by column chromatography (ethyl acetate/heptane 1:12)

Sources & evidence

ORD record
ord-3850ab0b2d26406f9b006cdc8f4462f5
Source dataset
uspto-grants-2014_11
Patent number
US08883829B2

Linked notes

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