Azobenzene → 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide

Participants

Role	Name	HCID	Charge
Reactant	Azobenzene	HCID 2272	—
Reactant	Dichlone	HCID 8342	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	Phenol, 2-[2-(4-chloro-2-nitrophenyl)diazenyl]-6-(1,1-dimethylethyl)-4-methyl-	HCID 89771	—
Reactant	(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal	HCID 107526	—
Solvent	Methanol	HCID 887	—
Product	2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide	HCID 14149470	—

Reaction Conditions

Temperature	65 °C

Reaction Steps

97% sodium hydroxide 8.2 g was added to methanol 100 ml, and the mixture was stirred at 65° C. for 30 minutes. After cooling to 50° C., 2-nitro-4-chloro-2'-hydroxy-3'-t-butyl-5'-methylazobenzene 11.6 g was added to the resultant mixture over 30 minutes, and thereafter 2,3-dichloro-1,4-naphthoquinone 0.7 g was added. Glucose 4 g was then added to the resultant mixture at 40° to 45° C. over one hour, and the mixture was further stirred for one hour at 40° to 45° C. As this result, almost all of the azobenzene disappeared to produce 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5-chlorobenzotriazole-N-oxide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04835284
Source dataset	uspto-grants-1989_05
ORD ID	ord-24edc5ffb8d6492c984d3d8adc627fbf
Source note	uspto-grants-1989_05