1,2,3-Trimethoxybenzene → (2-Hydroxy-3,4-dimethoxyphenyl)-(3,4,5-trimethoxyphenyl)methanone

HRID 2378182Notes

Reaction equation

HRID 2378182 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[C:19]=1[O:26][CH3:27].[Cl-].[Al+3].[Cl-].[Cl-].COC1C=CC(OC)=CC=1C(C1C=C(OC)C=C(OC)C=1)=O>C(Cl)Cl>[OH:24][C:20]1[C:19]([O:26][CH3:27])=[C:18]([O:17][CH3:16])[CH:23]=[CH:22][C:21]=1[C:6]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:7]

Participants

6

Reactant 4

HCID 124621,2,3-TrimethoxybenzeneHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 6451240Aluminum(III) ChlorideHCID 69203595(2,5-Dimethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanone

Product 1

HCID 69204157(2-Hydroxy-3,4-dimethoxyphenyl)-(3,4,5-trimethoxyphenyl)methanoneYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,4,5-Trimethoxybenzoyl chloride (11.07 g, 48.0 mmol), 1,2,3-trimethoxybenzene (8.07 g, 48.0 mmol) in anhydrous methylene chloride (60 ml), and aluminum chloride (7.04 g, 52.8 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 (25% EtOAc in hexane) to give (2-hydroxy-3,4-dimethoxy-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone as a yellow solid (9.44 g, 54%); mp, 135-137° C.: 1HNMR (DMSO-d6) δ 11.39 (s, 1H, OH), 7.35 (d, J=8 Hz, 1H, Ar), 6.97 (s, 2H, Ar), 6.70 (d, J=9 Hz, 1H, Ar), 3.89 (s, 3H, OCH3), 3.81 (s, 6H, 2OCH3), 3.76 (s, 3H, OCH3), 3.74 (s, 3H, OCH3); 13C NMR (DMSO-d6) δ 197.5, 157.6, 154.6, 152.5, 140.8, 136.0, 132.9, 128.7, 115.8, 106.7, 103.6, 60.1, 60.0, 56.0; Anal. Calcd. For C18H20O7: C, 62.06; H, 5.79. Found: C, 62.05; H, 5.55. The product was carried over to the next step.

Workup

  1. customThe crude material was purified via flash column chromatography (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-5aca67ea5dc9457896ad3ca13a74017c
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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