Veratrole → 3,4-Dimethoxy-4'-phenylbenzophenone

HRID 366617ノート

反応式

HRID 366617 の反応式
CO[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1OC)[C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:7].[C:23]1(OC)[C:24](=[CH:27][CH:28]=[CH:29][CH:30]=1)OC.[Cl-].[Al+3].[Cl-].[Cl-].C1(C2C=CC=CC=2)C=CC(C(Cl)=O)=CC=1>>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[O:14][CH3:15])[C:6]([C:5]1[CH:4]=[CH:3][C:20]([C:23]2[CH:24]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:19][CH:18]=1)=[O:7]

参加物

5

反応物 4

HCID 7043VeratroleHCID 841514-Phenylbenzoyl chlorideHCID 223042Bis(3,4-dimethoxyphenyl)methanoneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 22887323,4-Dimethoxy-4'-phenylbenzophenone

実験手順

3,4-Dimethoxy-4'-phenylbenzophenone was prepared analogously to 3,4,3',4'-tetramethoxybenzophenone using veratrole (2.4 g, 17 mmol), aluminum chloride (2.5 g, 19 mmol) and 4-biphenylcarbonyl chloride (4 g, 18 mmol) with a reaction time of 24 hours at room temperature. The crude product was purified by flash column chromatography (silica gel, 2% ethyl acetate/methylene chloride) to afford 3.86 g (70%) of the product as a white solid: mp 103-104° C.; 1H NMR (CDCl3) δ 7.88-7.84 (m, 2 H), 7.73-7.64 (m, 4 H), 7.52-7.40 (m, 5 H), 6.93-6.90 (m, 1 H), 3.97 (s, 3 H), 3.96 (s, 3 H); 13C NMR (CDCl3) δ 194.9, 152.9, 148.9, 144.5, 139.8, 136.8, 130.2, 130.2, 128.8, 127.9, 127.1, 126.7, 125.2, 112.0, 109.7, 55.9, 55.9; Anal. Calcd for C21H18O3. Theoretical: C, 79.23; H, 5.70. Found: C, 78.91; H, 5.87.

後処理

  1. customwith a reaction time of 24 hours
  2. customat room temperature
  3. customThe crude product was purified by flash column chromatography (silica gel, 2% ethyl acetate/methylene chloride)

出典と根拠

ORDレコード
ord-06c3268590be41a593b840ea02bca7c4
出典データセット
uspto-grants-2000_10
特許番号
US06130226

反応ノート

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