Veratrole → (3,4-Dimethoxyphenyl)(4-nitrophenyl)methanone

HRID 1017934Notes

Reaction equation

HRID 1017934 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+]([O-])=O)[CH:9]=1)=[O:7].C1(OC)C(=CC=CC=1)OC.[Cl-].[Al+3].[Cl-].[Cl-].[N+:36](C1C=CC(C(Cl)=O)=CC=1)([O-:38])=[O:37]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:6]([C:8]1[CH:9]=[CH:10][C:11]([N+:36]([O-:38])=[O:37])=[CH:12][CH:13]=1)=[O:7]

Participants

5

Reactant 4

HCID 7043VeratroleHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10803185(3,4-Dimethoxyphenyl)(3-nitrophenyl)methanone

Product 1

HCID 13954267(3,4-Dimethoxyphenyl)(4-nitrophenyl)methanone

Procedure

3,4-Dimethoxy-4′-nitrobenzophenone was prepared analogously to 3,4-dimethoxy-3′-nitrobenzophenone using veratrole (3.8 mL, 30 mmol), aluminum chloride (4.4 g, 33 mmol) and 4-nitrobenzoyl chloride (5.7 g, 30 mmol) with a reaction time of 48 hours at reflux. The crude mixture was purified by flash column chromatography (silica gel, 4% ethyl acetate/methylene chloride) to afford 1.69 g (78%) of the product as a white solid: mp 172-173° C.; 1H NMR (CDCl3) δ 8.43-8.31 (m, 2 H), 7.97-7.86 (m, 2 H), 7.55-7.46 (m, 1 H), 7.40-7.30 (m, 1 H), 7.00-6.89 (m, 1 H), 3.99 (s, 3 H), 3.96 (s, 3 H); 13C NMR (CDCl3) δ 193.4, 153.8, 149.4, 149.3, 143.8, 130.2, 130.0, 125.8, 123.4, 111.7, 109.9, 56.1, 56.0; Anal. Calcd for C15H13NO5. Theoretical: C, 62.72; H, 4.56; N, 4.88. Found: C, 62.49; H, 4.68; N, 4.86.

Workup

  1. customwith a reaction time of 48 hours
  2. temperatureat reflux
  3. customThe crude mixture was purified by flash column chromatography (silica gel, 4% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-0ba5cbe59b9742f1bfa1ab6aa4f571e1
Source dataset
uspto-grants-2002_11
Patent number
US06479554B2

Reaction notes

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