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

반응식

[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]

참가 물질

반응물 4

HCID 1118Sulfuric Acid

HCID 6344Dichloromethane

HCID 10557Methallyl alcohol

HCID 111055374-Amino-2,3,5-trimethylphenol

생성물 1

HCID 102204225-Amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran hydrochloride수율 14.4%

실험 절차

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.