1,2,3-Trimethoxybenzene → (3,5-Dimethoxyphenyl)-(2-hydroxy-3,4-dimethoxyphenyl)methanone

HRID 2378179Notes

Reaction equation

HRID 2378179 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6](Cl)=[O:7].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[C:17]=1[O:24][CH3:25].[Cl-].[Al+3].[Cl-].[Cl-].COC1C=CC(OC)=CC=1C(C1C=C(OC)C=C(OC)C=1)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[C:17]([O:24][CH3:25])[C:18]=2[OH:22])=[O:7])[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1

Participants

6

Reactant 4

HCID 124621,2,3-TrimethoxybenzeneHCID 870033,5-Dimethoxybenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 69203595(2,5-Dimethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanone

Product 1

HCID 69205198(3,5-Dimethoxyphenyl)-(2-hydroxy-3,4-dimethoxyphenyl)methanoneYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Dimethoxybenzoyl chloride (5.19 g, 25.87 mmol), 1,2,3-trimethoxybenzene (4.35 g, 25.87 mmol) in anhydrous methylene chloride (40 ml), and aluminum chloride (3.79 g, 28.45 mmol) were treated in the same manner as described above for the synthesis of (2,5-dimethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanone. The crude material was purified via flash column chromatography (20% EtOAc in hexane) to give (3,5-dimethoxy-phenyl)-(2-hydroxy-3,4-dimethoxy-phenyl)-methanone as a yellow solid (4.15 g, 50%); 1HNMR (CDCl3) δ 12.36 (s, 1H, OH), 7.42 (d, J=9 Hz, 1H, Ar), 6.75 (d, J=2 Hz, 2H, Ar), 6.64 (t, J=2 Hz, 1H, Ar), 6.47 (d, J=9 Hz, 1H, Ar), 3.94 (s, 6H, 2OCH3), 3.84 (s, 6H, 2OCH3); 13C NMR (CDCl3) δ 200.4, 160.7, 158.9, 158.0, 140.1, 136.9, 130.3, 114.6, 107.0, 103.8, 102.9, 60.9, 56.3, 55.7; Anal. Calcd. For C17H8O6: C, 64.14; H, 5.70. Found: C, 64.29; H, 5.42; N, <0.05. The product was carried over to the next step.

Workup

  1. customThe crude material was purified via flash column chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-4c78c7f23124487d801d962249b33be7
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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