Sulfuric Acid → 2-(2'-Hydroxy-methylphenyl) benzotriazole

HRID 257651

反応式

HRID 257651 の反応式
[OH-].[Na+].[O:3]=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.O[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[N:23]1[N+:27]([O-])=[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]2=[N:24]1.S(=O)(=O)(O)O>C1C2C(=O)C3C(=CC=CC=3)C=2C=CC=1.O.CO>[OH:3][C:18]1[C:19]([CH3:22])=[CH:20][CH:21]=[CH:16][C:17]=1[N:23]1[N:27]=[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]2=[N:24]1

参加物

8

反応物 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 132146462-(2-hydroxy-5-methylphenyl)benztriazole N-oxide

生成物 1

HCID 135808092-(2'-Hydroxy-methylphenyl) benzotriazole収率 92.8%

試薬・触媒・溶媒 3

HCID 10241Fluorenone触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To the wet product 12 g (~ 0.4 mol) thus obtained, is added methanol (60 ml), water (30 ml), 97% sodium hydroxide (13.0 g) and 9-fluorenone (0.5 g), and glucose (5.5 g) (0.3 mol) is further added to the mixture over an hour while stirring at 50° to 55° C. The mixture is reacted while stirring at 75° C. (boiling point) for 5 hours. As a result, the N-oxide disappears. The reaction liquor is neutralized with 62% sulfuric acid (19.8 g) to pH 8 to precipitate a crystal. The precipitated crystal is separated by filtration, and the separated crystal is fully washed with water and further with methanol. The washed crystal is then dried, thus obtaining 9.4 g of 2-(2'-hydroxy-methylphenyl) benzotriazole having a melting point of 128 to 130° C. at the yield of 92.8%. One can see that the reduction with aromatic ketones takes over 9 hours to complete. This reduction also required the use of two catalysts and a greater amount of total catalysts.

後処理

  1. additionis further added to the mixture over an hour
  2. customThe mixture is reacted
  3. stirringwhile stirring at 75° C. (boiling point) for 5 hours
  4. customto precipitate a crystal
  5. customThe precipitated crystal is separated by filtration
  6. washthe separated crystal is fully washed with water and further with methanol
  7. customThe washed crystal is then dried

出典と根拠

ORDレコード
ord-adf81cdb482147bb8d95ef8e5d349c21
出典データセット
uspto-grants-1993_11
特許番号
US05262541

関連ノート

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