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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 273899Erstellt: 25. Oktober 2026

P-Cymene → 2-(Benzotriazol-2-yl)-4-methyl-6-(2-hydroxy-3-benzoyl-6-n-octyloxybenzyl)phenol

https://huagongshe.com/reaction/273899

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktP-CymeneHCID 7463—
EduktOctabenzoneHCID 15797—
EduktSodium MethoxideHCID 10942334—
Edukt2-(2-Hydroxy-3-diethylaminomethyl-5-methylphenyl)-2H-benzotriazoleHCID 15919022—
Produkt2-(Benzotriazol-2-yl)-4-methyl-6-(2-hydroxy-3-benzoyl-6-n-octyloxybenzyl)phenolHCID 1991727033,1%

Reaktionsschritte

2-(2-Hydroxy-3-diethylaminomethyl-5-methylphenyl)-2H-benzotriazole (21.0 g, 0.067 mol), 2-hydroxy-4-n-octyloxybenzophenone (22.0 g, 0.067 mol), and p-cymene (80 g) are charged to a reaction flask. The mixture is heated to dissolve, and sodium methoxide (1.0 g, 25% in methanol) is added as catalyst. The solution is heated with agitation under a nitrogen flow at reflux (176°-178° C.) for 24 hours. After cooling to room temperature, the solution is filtered, and the black filtered solid (~1 g) is discarded. The product is then precipitated with methanol. The yellow solid (12.5 g) obtained is vacuum filtered, and identified using thin layer chromatography, with toluene:acetone (1:1) as the mobile phase. To remove the yellow color, the solid product is dissolved in hot toluene, and silica gel is introduced. The silica gel is gravity filtered hot. The toluene is removed by vacuum distillation, yielding 8.2 g of the title compound as an off-white solid, m.p. 124°-126° C. H NMR shows proton resonances at 0.73 ppm, triplet, 3 protons, (terminal --CH3 in --OC8H17); 1.06-1.24 ppm, complex, 8 protons, (inner 4X-CH2 in --OC8H17); 1.32 ppm, quintet, 2 protons, (--CH2 beta to Ar--O); 1.71 ppm, quintet, 2 protons, (--CH2 gamma to Ar--O); 2.32 ppm, singlet, 3 protons (--CCH3); 4.03 ppm, triplet, 2 protons, (--CH2 alpha to Ar-0); 4.24 ppm, singlet, 2 protons, (Ar--CH2 --Ar); 6.48 ppm, doublet, 1 proton, (C8H17OCCH--); 6.82 ppm, 1 proton, (CH3CCHC--CH2 --Ar); 7.40-7.64 ppm, complex, 6 protons, (Ar--COCCHCH3 --, C8H17OCCHCH--,--NCCHC2H2 --); 7.68 ppm, doublet, 2 protons, (AR--COCCHC3H3CH), 7.95 ppm, complex, 2 protons, (--NCCHC2H2CH); 8.05 ppm, 1 proton, (CH3CCHCNCOH); 11.46 and 12.80 ppm, two singlets, two protons, (exchangeable --OH protons).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05387691
Quelldatensatzuspto-grants-1995_02
ORD IDord-82f3236b296c4950864fa36cb66b9ae8
Quellennotizuspto-grants-1995_02