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

HRID 2296838

Reaktionsgleichung

Reaktionsgleichung von HRID 2296838
[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

Komponenten

6

Edukt 3

HCID 6568(+-)-2-ButanolHCID 14798Sodium HydroxideHCID 70118378HCID 70118378, Verbindung

Produkt 1

HCID 120106532-[2-Hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzotriazoleAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8342DichloneKatalysatorHCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

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 tide 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4f90a3fe32814f20b047e65bb0f412b9
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489383B1

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