Veratrole → Methanone, (3,4-dimethoxyphenyl)(3-methoxyphenyl)-

HRID 2378229Notes

Reaction equation

HRID 2378229 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21].[Cl-].[Al+3].[Cl-].[Cl-].COC1C=C(C(C2C=CC(OC)=CC=2)=CC#N)C=CC=1OC>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:6]([C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:7])[CH:17]=[CH:16][C:15]=1[O:20][CH3:21]

Participants

6

Reactant 4

HCID 7043VeratroleHCID 74374m-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 692026013-(3,4-Dimethoxy-phenyl)-3-(4-methoxy-phenyl)-acrylonitrile

Product 1

HCID 11032987Methanone, (3,4-dimethoxyphenyl)(3-methoxyphenyl)-Yield 110%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-methoxybenzoyl chloride (2.06 ml, 14.65 mmol), 1,2-dimethoxybenzene (1.87 ml, 14.65 mmol) in anhydrous methylene chloride (25 ml), and aluminum chloride (2.15 g, 16.12 mmol) were treated in the same manner as described above for the synthesis of 3-(3,4-dimethoxy-phenyl)-3-(4-methoxy-phenyl)-acrylonitrile. The crude was purified via flash column chromatography (20% EtOAc in hexane) to give (3,4-dimethoxy-phenyl)-(3-methoxy-phenyl)-methanone as a yellow oil (4.39 g, 100%); 1HNMR (CDCl3) δ 7.50 (d, J=1 Hz, 1H, Ar), 7.42-7.30 (m, 4H, Ar), 7.14-7.09 (m, 1H, Ar), 6.90 (d, J=8 Hz, 1H, Ar), 3.96 (s, 3H, OCH3), 3.95 (s, 6H, 2OCH3), 3.86 (s, 3H, OCH3); 13C NMR (CDCl3) δ 195.4, 159.6, 153.1, 149.1, 139.7, 130.3, 129.2, 125.6, 122.5, 118.3, 114.4, 112.3, 109.9, 56.2, 56.2, 55.6; Anal. Calcd. For C16H16O4: C, 70.58; H, 5.92. Found: C, 70.38; H, 5.99; N, <0.05. The product was carried over to the next step.

Workup

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

Sources & evidence

ORD record
ord-e67942acd423448a85e1af784b48f178
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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