Sodium Hydroxide → 2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

HRID 234252

Reaktionsgleichung

Reaktionsgleichung von HRID 234252
[CH3:1][C:2]1([CH3:24])[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[C:5]2[C:14]([CH3:23])=[C:15]([N+:20]([O-])=O)[C:16]([CH3:19])=[C:17]([CH3:18])[C:4]=2[O:3]1.[OH-].[Na+]>CO.[Zn]>[NH2:20][C:15]1[C:16]([CH3:19])=[C:17]([CH3:18])[C:4]2[O:3][C:2]([CH3:24])([CH3:1])[CH:6]([C:7]3[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=3)[C:5]=2[C:14]=1[CH3:23]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 104962842,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-5-nitro-2,3-dihydrobenzofuran

Produkt 1

HCID 106853092,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amineAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-5-nitro-2,3-dihydrobenzofuran (1.26 g, 3.9 mmol) was dissolved in methanol (30 ml). Zinc powder (1.3 g) and 1N sodium hydroxide (15 ml) were added to the solution and the mixture was heated under reflux for 3 hours. Insoluble materials were filtered off and water was added. The mixture was extracted with ethyl acetate. The extract was washed with water, dried and then the solvent was distilled off. The residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 95:5) and crystallized from hexane to obtain the desired compound (710 mg, yield: 53.7%), m.p. 119°-120° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationInsoluble materials were filtered off
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 95:5)
  10. customcrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-5e5275d0e210400bb4942d2d6f45ab88
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594154

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