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

HRID 46710

反応式

HRID 46710 の反応式
[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

参加物

12

反応物 8

HCID 313Hydrochloric Acid2 回HCID 996PhenolHCID 69462-NitroanilineHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide3 回HCID 12370884-(Benzotriazol-2-yl)phenolHCID 203862814,4'-Bis(2-bromoethoxy)-2-hydroxybenzophenoneHCID 23668193Sodium Nitrite

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1cf0070342a943b8a1c94b6333f874f6
出典データセット
uspto-grants-1979_11
特許番号
US04174321

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