1,2,3-Trimethoxybenzene → (3,5-Dimethoxyphenyl)-(2-hydroxy-3,4-dimethoxyphenyl)methanone

HRID 970972노트

반응식

HRID 970972 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6](Cl)=[O:7].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[C:17]=1[O:24][CH3:25].[Cl-].[Al+3].[Cl-].[Cl-].COC1C=CC(OC)=CC=1C(C1C=C(OC)C=C(OC)C=1)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[C:17]([O:24][CH3:25])[C:18]=2[OH:22])=[O:7])[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1

참가 물질

6

반응물 4

HCID 124621,2,3-TrimethoxybenzeneHCID 870033,5-Dimethoxybenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 69203595(2,5-Dimethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanone

생성물 1

HCID 69205198(3,5-Dimethoxyphenyl)-(2-hydroxy-3,4-dimethoxyphenyl)methanone수율 50.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3,5-Dimethoxybenzoyl chloride (5.19 g, 25.87 mmol), 1,2,3-trimethoxybenzene (4.35 g, 25.87 mmol) in anhydrous methylene chloride (40 ml), and aluminum chloride (3.79 g, 28.45 mmol) were treated in the same manner as described above for the synthesis of (2,5-dimethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanone. The crude material was purified via flash column chromatography (20% EtOAc in hexane) to give (3,5-dimethoxy-phenyl)-(2-hydroxy-3,4-dimethoxy-phenyl)-methanone as a yellow solid (4.15 g, 50%); 1HNMR (CDCl3) δ 12.36 (s, 1H, OH), 7.42 (d, J=9 Hz, 1H, Ar), 6.75 (d, J=2 Hz, 2H, Ar), 6.64 (t, J=2 Hz, 1H, Ar), 6.47 (d, J=9 Hz, 1H, Ar), 3.94 (s, 6H, 2OCH3), 3.84 (s, 6H, 2OCH3); 13C NMR (CDCl3) δ 200.4, 160.7, 158.9, 158.0, 140.1, 136.9, 130.3, 114.6, 107.0, 103.8, 102.9, 60.9, 56.3, 55.7; Anal. Calcd. For C17H18O6: C, 64.14; H, 5.70. Found: C, 64.29; H, 5.42; N, <0.05. The product was carried over to the next step.

후처리

  1. customThe crude material was purified via flash column chromatography (20% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-f25e9a51b74b4af88553208e4ca13cd9
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312241B2

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