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Hydrochloric Acid → 4,4'-bis[2-[4-(2H-benzotriazol-2 yl)phenoxy]ethoxy]-2-hydroxybenzophenone

HRID 46710
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HRID 46710 반응식
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.Cl.[N:12]([O-])=O.[Na+].[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].[N:25]1[N:26]([C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)[N:27]=[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=12.Br[CH2:42][CH2:43][O:44][C:45]1[CH:62]=[CH:61][C:48]([C:49]([C:51]2[CH:56]=[CH:55][C:54]([O:57][CH2:58][CH2:59]Br)=[CH:53][CH:52]=2)=[O:50])=[C:47]([OH:63])[CH:46]=1.C(=O)([O-])[O-].[K+].[K+]>[Zn].CC(CC)=O.O>[N:1]1[N:12]([C:19]2[CH:20]=[CH:21][C:16]([O:22][CH2:42][CH2:43][O:44][C:45]3[CH:62]=[CH:61][C:48]([C:49]([C:51]4[CH:56]=[CH:55][C:54]([O:57][CH2:58][CH2:59][O:40][C:37]5[CH:38]=[CH:39][C:34]([N:26]6[N:27]=[C:28]7[CH:33]=[CH:32][CH:31]=[CH:30][C:29]7=[N:25]6)=[CH:35][CH:36]=5)=[CH:53][CH:52]=4)=[O:50])=[C:47]([OH:63])[CH:46]=3)=[CH:17][CH:18]=2)[N:6]=[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

12

반응물 8

HCID 313Hydrochloric Acid2회HCID 996PhenolHCID 69462-NitroanilineHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide3회HCID 12370884-(Benzotriazol-2-yl)phenolHCID 203862814,4'-Bis(2-bromoethoxy)-2-hydroxybenzophenone
HCID 23668193
Sodium Nitrite

생성물 1

HCID 203863034,4'-bis[2-[4-(2H-benzotriazol-2 yl)phenoxy]ethoxy]-2-hydroxybenzophenone

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 962Water용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

o-Nitroaniline (138 g.) was diazotized in the usual manner with concentrated hydrochloric acid (400 ml.), water (200 ml.) and sodium nitrite (72 g.). The clear diazonium solution was added slowly to a cold solution of phenol (94 g.) in 900 ml. of 10% sodium hydroxide. The mixture was stirred for one hour and filtered, yielding 136 g. (56%) of the diazo compound (m.p. 154°-158° C.). This product was dissolved in 650 ml. of 2N sodium hydroxide solution. Zinc dust (130 g.) and sodium hydroxide (100 ml. of a 25% solution) were added slowly to the well-stirred solution. The mixture was cooled to <30° C. and acidified with concentrated hydrochloric acid. After stirring for 2 hours, the precipitate was filtered. The precipitate was taken up in a 1 liter filter of hot ethanol, solution filtered, cooled and product, p-(2H-benzotriazol2-yl)phenol, filtered out (m.p. 216°-218° C.). A well stirred mixture of p-(2H-benzotriazol-2-yl)phenol (0.02 mole), 4,4'-bis(2-bromoethoxy)-2-hydroxybenzophenone (0.01 mole), potassium carbonate (0.02 mole) and 200 ml. of methyl ethylketone were refluxed for 16 hours. The reaction mixture was washed with water. After the solvent was removed on a steam bath, 4,4'-bis[2-[4-(2H-benzotriazol-2 yl)phenoxy]ethoxy]-2-hydroxybenzophenone was obtained.

후처리

  1. filtrationfiltered
  2. customyielding 136 g
  3. dissolutionThis product was dissolved in 650 ml
  4. temperatureThe mixture was cooled to <30° C.
  5. stirringAfter stirring for 2 hours
  6. filtrationthe precipitate was filtered
  7. filtrationfilter of hot ethanol, solution
  8. filtrationfiltered
  9. temperaturecooled
  10. filtrationproduct, p-(2H-benzotriazol2-yl)phenol, filtered out (m.p. 216°-218° C.)
  11. stirringA well stirred
  12. washThe reaction mixture was washed with water
  13. customAfter the solvent was removed on a steam bath

출처 및 근거

ORD 기록
ord-1cf0070342a943b8a1c94b6333f874f6
출처 데이터셋
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04174321

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