2,6-Di-tert-butyl-4-methylphenol → Phenol, 4-(bromomethyl)-2,6-bis(1,1-dimethylethyl)-

Participants

Reaction Steps

A mixture of 2,6-di-tert-butyl-4-methylphenol (2.34 g), N-bromosuccinimide (1.88 g) and carbon tetrachloride (25 ml) was refluxed for 2 hrs. The mixture was filtered to remove the insoluble precipitate to give a solution of 4-bromomethyl-2,6-di-tert-butylphenol. To the solution was added 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (2.0 g), and the whole was stirred for 5 hrs. at room temperature. The mixture was diluted with chloroform, washed with water, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by a column chromatography on silica gel and recrystallized from a mixture of acetone and isopropyl ether to give 4-(2-chlorophenyl)-3-(2,6-di-tert-butyl-4-hydroxyphenyl)amino-6,8-dimethylquinoline as colorless prisms (1.59 g, 44.9%). m.p. 183°-185° C.

Provenance & Evidence