Sulfuric Acid → 5-Amino-2-benzyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran

HRID 964788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 964788
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([OH:14])=[C:9]([CH3:15])[C:8]=1[CH3:16].[CH3:17][C:18](=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)CO.[C:28](=O)(O)[O-].[Na+]>ClCCl>[NH2:6][C:7]1[C:12]([CH3:13])=[C:11]([CH3:28])[C:10]2[O:14][C:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([CH3:17])[CH2:15][C:9]=2[C:8]=1[CH3:16]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5608792-Methyl-3-phenyl-2-propen-1-olHCID 111055374-Amino-2,3,5-trimethylphenol

Produkt 1

HCID 158169895-Amino-2-benzyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuranAusbeute 19,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sulfuric acid (15 ml) was added to a solution of 4-amino-2,3,5-trimethylphenol (20.0 g, 0.13 mol) and 2-methyl-3-phenyl-2-propenol (25.0 g, 0.17 mol) in dichloromethane (100 ml) and the mixture was heated under reflux for 1 hour. The resulting reaction mixture was neutralized with aqueous saturated sodium bicarbonate solution and the product was extracted with ethyl acetate. The extract was washed with water and dried and then the solvent was distilled off. The residue was purified by silica gel column chromatography (isopropyl ether) and crystallized from hexane to obtain the desired compound (7.2 g, yield: 19.3%), m.p. 68°-69° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe resulting reaction mixture
  4. extractionthe product was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (isopropyl ether)
  9. customcrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-905b45e7a61e4dd18e000ba62e17e448
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05770772

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