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

HRID 273899

반응식

HRID 273899 반응식
[OH:1][C:2]1[C:7]([CH2:8]N(CC)CC)=[CH:6][C:5]([CH3:14])=[CH:4][C:3]=1[N:15]1[N:19]=[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]2=[N:16]1.[OH:24][C:25]1[CH:38]=[C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:36]=[CH:35][C:26]=1[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28].CC1C=CC(C(C)C)=CC=1.C[O-].[Na+]>>[N:16]1[N:15]([C:3]2[CH:4]=[C:5]([CH3:14])[CH:6]=[C:7]([CH2:8][C:38]3[C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:36][CH:35]=[C:26]([C:27](=[O:28])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:25]=3[OH:24])[C:2]=2[OH:1])[N:19]=[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=12

참가 물질

5

반응물 4

HCID 7463P-CymeneHCID 15797OctabenzoneHCID 10942334Sodium MethoxideHCID 159190222-(2-Hydroxy-3-diethylaminomethyl-5-methylphenyl)-2H-benzotriazole

생성물 1

HCID 199172702-(Benzotriazol-2-yl)-4-methyl-6-(2-hydroxy-3-benzoyl-6-n-octyloxybenzyl)phenol수율 33.1%

실험 절차

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).

후처리

  1. temperatureThe mixture is heated
  2. dissolutionto dissolve
  3. temperatureThe solution is heated with agitation under a nitrogen flow
  4. temperatureat reflux (176°-178° C.) for 24 hours
  5. filtrationthe solution is filtered
  6. filtrationthe black filtered solid (~1 g)
  7. customThe product is then precipitated with methanol

출처 및 근거

ORD 기록
ord-82f3236b296c4950864fa36cb66b9ae8
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387691

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