Veratrole → 3,4-Dimethoxybenzophenone

HRID 1017921노트

반응식

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]

참가 물질

반응물 4

HCID 7043Veratrole

HCID 7412Benzoyl chloride

HCID 223042Bis(3,4-dimethoxyphenyl)methanone

HCID 6451240Aluminum(III) Chloride

생성물 1

HCID 2867423,4-Dimethoxybenzophenone

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록: ord-ca526c6989264faa957ade5d6a0a1564
출처 데이터셋: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06479554B2

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