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

HRID 970972ノート

反応式

HRID 970972 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f25e9a51b74b4af88553208e4ca13cd9
出典データセット
uspto-grants-2007_12
特許番号
US07312241B2

反応ノート

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