(+-)-2-Butanol → 2-[2-Hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzotriazole

HRID 1937062

反応式

HRID 1937062 の反応式
[OH-].[Na+].CC(O)CC.[OH:8][C:9]1[C:14]([C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])=[CH:13][C:12]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:11][C:10]=1[N:33]1[N+:37]([O-])=[C:36]2[CH:39]=[CH:40][CH:41]=[CH:42][C:35]2=[N:34]1>ClC1C(=O)C2C(C(=O)C=1Cl)=CC=CC=2.CC(=O)CC>[OH:8][C:9]1[C:14]([C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16])=[CH:13][C:12]([C:29]([CH3:30])([CH3:31])[CH3:32])=[CH:11][C:10]=1[N:33]1[N:37]=[C:36]2[CH:39]=[CH:40][CH:41]=[CH:42][C:35]2=[N:34]1

参加物

6

反応物 3

HCID 6568(+-)-2-ButanolHCID 14798Sodium HydroxideHCID 70118378HCID 70118378、化合物

生成物 1

HCID 120106532-[2-Hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzotriazole収率 96.7%

試薬・触媒・溶媒 2

HCID 8342Dichlone触媒HCID 6569Methyl Ethyl Ketone溶媒

反応条件

温度
82 °C

実験手順

To a 500 mL three-necked flask fitted with a mechanical stirrer, 3 g of sodium hydroxide pellets and 50 mL of 2-butanol are charged and heated to 82° C. To this solution, a slurry of 200 mL of 2-butanone, 15 g of the benzotriazole N-oxide prepared in Example 4, and 0.67 g of 2,3-dichloro-1,4-naphthoquinone is added over 40 minutes. The mixture is refluxed at 88° C. for five hours while distilling off 2-butanone. Additional 2-butanol (50 mL) is added to replace what is lost during distillation of the 2-butanone. After cooling the reaction mixture to ambient temperature, 25 g of water and 30 mL of ethyl acetate are added at which time the pH is reduced to 2 with 30% aqueous sulfuric acid. After splitting off the aqueous layer, the solvent is removed by distillation and the crude solid purified by silica gel chromatography using heptane/ethyl acetate as the eluent. After collecting the desired fractions and crystallization from methanol/toluene, 14 g of the title compound is obtained after drying as a light yellow solid melting at 172-173° C. The structure is confirmed by 1H nmr and mass spectroscopy.

後処理

  1. customTo a 500 mL three-necked flask fitted with a mechanical stirrer
  2. temperatureThe mixture is refluxed at 88° C. for five hours
  3. distillationwhile distilling off 2-butanone
  4. additionAdditional 2-butanol (50 mL) is added
  5. distillationis lost during distillation of the 2-butanone
  6. temperatureAfter cooling the reaction mixture to ambient temperature
  7. addition25 g of water and 30 mL of ethyl acetate are added at which time the pH
  8. customthe solvent is removed by distillation
  9. customthe crude solid purified by silica gel chromatography
  10. customAfter collecting the desired
  11. customfractions and crystallization from methanol/toluene

出典と根拠

ORDレコード
ord-2180214673fb48aa92ad9ae38b604c7d
出典データセット
uspto-grants-2002_05
特許番号
US06392056B1

関連ノート

読み込み中…