Sulfuric Acid → Tinuvin

HRID 257654

반응식

HRID 257654 반응식
[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]([CH3:12])=[CH:4][C:3]=1[N:13]1[N+:17]([O-])=[C:16]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]2=[N:14]1.S(=O)(=O)(O)O>O>[OH:1][C:2]1[C:7]([C:8]([CH3:10])([CH3:9])[CH3:11])=[CH:6][C:5]([CH3:12])=[CH:4][C:3]=1[N:13]1[N:17]=[C:16]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]2=[N:14]1

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 141494702-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide

생성물 1

HCID 62531Tinuvin수율 82.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Example 4 from U.S. Pat. No. 4,835,284 is duplicated. 97% sodium hydroxide (8.2 g) is added and dissolved in a mixture of methanol (60 ml) and water (20 ml). 2-nitro-4-chloro-2'-hydroxy-3'-t-butyl-5'-methylazobenzene (11.6 g) is then added to the resultant solution at 50° to 60° C. over 30 minutes while stirring, and thereafter 2,3-dichloro-1,4-naphthoquinone (0.3 g) and 9-fluorenone (0.4 g) are added to the solution. Glucose (8 g) is then added to the resultant mixture at 40° to 50° C. over two hours, and the mixture is stirred for one hour at the same temperature. As this result, almost all of the azobenzene disappears to produce 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide. The system is heated, and is stirred at 66° to 68° C. (boiling point) for 5 hours. As this result, the N-oxide disappears. Thereafter, water (50 ml) is added to the reaction liquor, and the resultant reaction liquor is neutralized with 62% sulfuric acid (10 g) to precipitate a crystal. The precipitated crystal is separated by filtration, and the separated crystal is fully washed with hot water of 60° to 70° C. and further with a small amount of methanol. The washed crystal is then dried, thus obtaining 8.7 g of 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5-chlorobenzotriazole having a melting point of 138° to 140° C. at the yield of 82.9%. One can see that the reaction using an aromatic ketone takes over 71/2 hours.

후처리

  1. temperatureThe system is heated
  2. customthe resultant reaction liquor
  3. customto precipitate a crystal
  4. customThe precipitated crystal is separated by filtration
  5. washthe separated crystal is fully washed with hot water of 60° to 70° C. and further with a small amount of methanol
  6. customThe washed crystal is then dried

출처 및 근거

ORD 기록
ord-fa620fbf0bfb412c834a2bf8192eb0ea
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262541

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