1,2,3-Trimethoxybenzene → (2-Hydroxy-3,4-dimethoxyphenyl)-(3,4,5-trimethoxyphenyl)methanone

HRID 2378182ノート

反応式

HRID 2378182 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[C:19]=1[O:26][CH3:27].[Cl-].[Al+3].[Cl-].[Cl-].COC1C=CC(OC)=CC=1C(C1C=C(OC)C=C(OC)C=1)=O>C(Cl)Cl>[OH:24][C:20]1[C:19]([O:26][CH3:27])=[C:18]([O:17][CH3:16])[CH:23]=[CH:22][C:21]=1[C:6]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:7]

参加物

6

反応物 4

HCID 124621,2,3-TrimethoxybenzeneHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 6451240Aluminum(III) ChlorideHCID 69203595(2,5-Dimethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanone

生成物 1

HCID 69204157(2-Hydroxy-3,4-dimethoxyphenyl)-(3,4,5-trimethoxyphenyl)methanone収率 56.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3,4,5-Trimethoxybenzoyl chloride (11.07 g, 48.0 mmol), 1,2,3-trimethoxybenzene (8.07 g, 48.0 mmol) in anhydrous methylene chloride (60 ml), and aluminum chloride (7.04 g, 52.8 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 (25% EtOAc in hexane) to give (2-hydroxy-3,4-dimethoxy-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone as a yellow solid (9.44 g, 54%); mp, 135-137° C.: 1HNMR (DMSO-d6) δ 11.39 (s, 1H, OH), 7.35 (d, J=8 Hz, 1H, Ar), 6.97 (s, 2H, Ar), 6.70 (d, J=9 Hz, 1H, Ar), 3.89 (s, 3H, OCH3), 3.81 (s, 6H, 2OCH3), 3.76 (s, 3H, OCH3), 3.74 (s, 3H, OCH3); 13C NMR (DMSO-d6) δ 197.5, 157.6, 154.6, 152.5, 140.8, 136.0, 132.9, 128.7, 115.8, 106.7, 103.6, 60.1, 60.0, 56.0; Anal. Calcd. For C18H20O7: C, 62.06; H, 5.79. Found: C, 62.05; H, 5.55. The product was carried over to the next step.

後処理

  1. customThe crude material was purified via flash column chromatography (25% EtOAc in hexane)

出典と根拠

ORDレコード
ord-5aca67ea5dc9457896ad3ca13a74017c
出典データセット
uspto-grants-2008_12
特許番号
US07470723B2

反応ノート

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