Sulfuric Acid → 5-Amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran hydrochloride

HRID 964789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 964789
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([CH3:10])[C:3]=1[CH3:11].[CH3:12][C:13](=C)[CH2:14]O.S(=O)(=O)(O)O.[Cl:22][CH2:23]Cl>>[ClH:22].[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:23])[C:5]2[O:9][C:13]([CH3:14])([CH3:12])[CH2:10][C:4]=2[C:3]=1[CH3:11]

Komponenten

5

Edukt 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 10557Methallyl alcoholHCID 111055374-Amino-2,3,5-trimethylphenol

Produkt 1

HCID 102204225-Amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran hydrochlorideAusbeute 14,4 %

Versuchsvorschrift

4-Amino-2,3,5-trimethylphenol (2.0 g, 13.2 mmol) and 2-methyl-2-propenol (1.15 g, 15.8 g) were heated under reflux in dichloromethane (20 ml) together with sulfuric acid (2 ml) for 18 hours. The reaction mixture was washed with aqueous saturated sodium bicarbonate solution, dried and then concentrated. The residue was purified by silica gel column chromatography (isopropyl ether). The purified product was converted into its hydrochloride and it was crystallized from ethanol-isopropyl ether to obtain the desired compound (460 mg, yield: 14.4%), m.p. 248°-250° C.

Aufarbeitung

  1. washThe reaction mixture was washed with aqueous saturated sodium bicarbonate solution
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (isopropyl ether)
  5. customwas crystallized from ethanol-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-40640889f61648528781dd96a8cd9e56
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05770772

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