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

HRID 366622노트

반응식

HRID 366622 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21]C)[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=CC2OCOC=2C=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][C:20]2[O:21][CH2:1][O:2][C:3]=2[CH:4]=1)=[O:7]

참가 물질

5

반응물 4

HCID 7043VeratroleHCID 223042Bis(3,4-dimethoxyphenyl)methanoneHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 6253753,4-Dimethoxy-3',4'-methylenedioxybenzophenone

실험 절차

1 -(3,4-Dimethoxybenzoyl)-3,4-methylenedioxybenzene was prepared analogously to 3,4,3',4'-tetramethoxybenzophenone using veratrole (1.3 mL, 10 mmol), aluminum chloride (1.5 g, 11 mmol) and piperonyloyl chloride (1.9 g, 10 mmol) with a reaction time of 2.5 hours at room temperature. The crude product was purified by flash column chromatography (silica gel, 5% ethyl acetate/methylene chloride) to afford 1.99 g (69%) of the product as a white solid: mp 164-165° C.; 1H NMR (CDCl3) δ 7.46-7.26 (m, 4 H), 6.95-6.82 (m, 2 H), 6.06 (s, 2 H), 3.96 (s, 3 H), 3.94 (s, 3 H); 13C NMR (CDCl3) δ 193.9, 152.7, 151.0, 148.9, 147.8, 132.4, 130.6, 126.1, 124.8, 112.2, 109.9, 109.7, 107.6, 101.7, 56.0, 56.0; Anal. Calcd for C16H14O5. Theoretical: C, 67.13; H, 4.93. Found: C, 66.86; H, 5.11.

후처리

  1. customwith a reaction time of 2.5 hours
  2. customat room temperature
  3. customThe crude product was purified by flash column chromatography (silica gel, 5% ethyl acetate/methylene chloride)

출처 및 근거

ORD 기록
ord-650704527abe40ae9b0c6783b79ce986
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130226

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