Veratrole → 3,4-Dimethoxybenzophenone

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].C1(OC)C(=CC=CC=1)OC.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(=O)C1C=CC=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:18]=[CH:19][CH:20]=[CH:3][CH:4]=1)=[O:7]

参加物

反応物 4

HCID 7043Veratrole

HCID 7412Benzoyl chloride

HCID 223042Bis(3,4-dimethoxyphenyl)methanone

HCID 6451240Aluminum(III) Chloride

生成物 1

HCID 2867423,4-Dimethoxybenzophenone

実験手順

3,4-Dimethoxybenzophenone was prepared analogously to 3,4,3′,4′-tetramethoxybenzophenone using veratrole (2 mL, 15 mmol), aluminum chloride (2.2 g, 16.5 mmol) and benzoyl chloride (1.8 mL, 15.5 mmol). The crude mixture was purified by flash column chromatography (silica gel, 3% ethyl acetate/methylene chloride) to yield 3.44 g (93%) of the product as a white solid: mp 99-100° C.; 1H NMR (CDCl3) δ 7.82-7.30 (m, 7 H), 6.95-6.85 (m, 1 H), 3.96 (s, 3 H), 3.94 (s, 3 H); 13C NMR (CDCl3) δ 195.5, 153.0, 149.0, 138.2, 131.8, 130.2, 129.6, 128.1, 125.4, 112.1, 109.7, 56.0, 56.0; Anal. Calcd for C15H14O3. Theoretical: C, 74.36; H, 5.82. Found: C, 74.21; H, 6.01.

後処理

customThe crude mixture was purified by flash column chromatography (silica gel, 3% ethyl acetate/methylene chloride)

出典と根拠

ORDレコード: ord-ca526c6989264faa957ade5d6a0a1564
出典データセット: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06479554B2

反応ノート

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