Sulfuric Acid → UV-328

HRID 257652

Reaktionsgleichung

Reaktionsgleichung von HRID 257652
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N:11][C:12]1[CH:17]=[C:16]([C:18]([CH2:21][CH3:22])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])[C:13]=1[OH:28])([O-])=O.[OH-].[Na+].C1C2C(=O)C3C(=CC=CC=3)C=2C=CC=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.S(=O)(=O)(O)O>O.CO>[OH:28][C:13]1[C:14]([C:23]([CH2:26][CH3:27])([CH3:25])[CH3:24])=[CH:15][C:16]([C:18]([CH2:21][CH3:22])([CH3:20])[CH3:19])=[CH:17][C:12]=1[N:11]1[N:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[N:1]1

Komponenten

8

Edukt 5

HCID 1118Sulfuric AcidHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 1041112-Nitro-2'-hydroxy-3',5'-bis(tert-amyl)azobenzeneHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Produkt 1

HCID 33263UV-328Ausbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Example 1 from U.S. Pat. No. 4,835,284 is duplicated. 2-nitro-2'-hydroxy-3',5'-di-t-amylazobenzene (12.8 g) is added to a mixture of methanol (41 g), water (10 g) and 97% sodium hydroxide (11 g), and the resultant mixture is stirred at 65° C. for 30 minutes. Thereafter, 9-fluorenone (2.0 g) and then glucose (12 g) are added to the mixture at 60° C. to 65° C. over 4 hours. The resultant mixture is further stirred for 4 hours at the boiling point (70° C.), thus completing the reduction reaction. Thereafter, water (50 ml) is added to the reaction liquor, and the reaction liquor is neutralized with 62% sulfuric acid (13 g). The liquor thus neutralized is cooled to 20° C. to precipitate a crystal. The crystal thus obtained is separated by filtration, and the separated crystal is fully washed with water and further with methanol. The washed crystal is then dried, thus producing 9.9 g of 2-(2'-hydroxy-3',5'-di-t-amylphenyl)-benzotriazole having a melting point of 77° to 79° C. at the yield of 85.0%. One can see that reduction using the aromatic ketone 9-fluorenone takes over 81/2 hours.

Aufarbeitung

  1. customthe reduction reaction
  2. customto precipitate a crystal
  3. customThe crystal thus obtained
  4. customis separated by filtration
  5. washthe separated crystal is fully washed with water and further with methanol
  6. customThe washed crystal is then dried

Quellen und Nachweise

ORD-Eintrag
ord-5f49b659648e41138f6f7932b8dde1fd
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262541

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