Veratrole → 1-(3,4-Dimethoxybenzoyl)naphthalene

HRID 366633노트

반응식

HRID 366633 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([C:8]1[CH:13]=[CH:12][C:11](OC)=[C:10](OC)[CH:9]=1)=[O:7].[C:23]1(OC)[C:24](=CC=[CH:29][CH:30]=1)OC.[Cl-].[Al+3].[Cl-].[Cl-].C1(C(Cl)=O)C2C(=CC=CC=2)C=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([C:8]1[C:9]2[C:10](=[CH:24][CH:23]=[CH:30][CH:29]=2)[CH:11]=[CH:12][CH:13]=1)=[O:7]

참가 물질

5

반응물 4

HCID 7043VeratroleHCID 701461-Naphthalenecarbonyl chlorideHCID 223042Bis(3,4-dimethoxyphenyl)methanoneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 222259771-(3,4-Dimethoxybenzoyl)naphthalene

실험 절차

1-(3,4-Dimethoxybenzoyl)naphthalene was prepared analogously to 3,4,3',4'-tetramethoxybenzophenone using veratrole (1.3 mL, 10 mmol), aluminum chloride (1.5 g, 11 mmol) and 1-naphthoyl chloride (1.5 mL, 10 mmol) with a reaction time of 24 hours at room temperature. The crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/methylene chloride) to afford 1.85 g (63%) of the product as a white solid: mp 92.5-94.5° C.; 1H NMR (CDCl3) δ 8.06-7.84 (m, 3 H), 7.80-7.39 (m, 5 H), 7.31-7.21 (m, 1 H), 6.84-6.74 (m, 1 H), 3.94 (s, 3 H), 3.91 (s, 3 H); 13C NMR (CDCl3) δ 196.6, 153.5, 149.0, 136.8, 133.6, 131.1, 130.9, 130.5, 128.2, 126.9, 126.7, 126.3, 126.3, 125.6, 124.3, 111.3, 109.7, 56.0, 55.9; Anal. Calcd for C19H16O3. Theoretical: C, 78.06; H, 5.52. Found: C, 77.97; H, 5.66.

후처리

  1. customwith a reaction time of 24 hours
  2. customat room temperature
  3. customThe crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/methylene chloride)

출처 및 근거

ORD 기록
ord-46266b8182b7452583ca388335ad4051
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130226

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