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

HRID 234250

반응식

HRID 234250 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

5

반응물 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 10557Methallyl alcoholHCID 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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c85de5899764bb1962a3d0000aeae6c
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594154

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