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

HRID 46710

Reaction equation

HRID 46710 reaction equation
[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

Participants

12

Reactant 8

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1cf0070342a943b8a1c94b6333f874f6
Source dataset
uspto-grants-1979_11
Patent number
US04174321

Linked notes

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