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

HRID 583449Notes

Reaction equation

HRID 583449 reaction equation
[C:1]1([O:9][CH3:10])[C:2](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:3][CH3:4].[Cl-].[Al+3].[Cl-].[Cl-].[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=[O:22])([O-:17])=[O:16].O>C(Cl)Cl>[CH3:4][O:3][C:2]1[CH:5]=[C:6]([CH:7]=[CH:8][C:1]=1[O:9][CH3:10])[C:21]([C:20]1[CH:24]=[CH:25][CH:26]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7043VeratroleHCID 8495Benzoyl chloride, 3-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 10803185(3,4-Dimethoxyphenyl)(3-nitrophenyl)methanoneYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred ice bath cooled solution of veratrole (2.55 mL, 20 mmol) in methylene chloride (30 mL) under nitrogen was added aluminum chloride (2.93 g, 22 mmol). A slight exotherm resulted. To the resulting mixture was added 3-nitrobenzoyl chloride (3.8 g, 20 mmol) in 30 mL of methylene chloride. The reaction was then allowed to warm to room temperature and followed by heating to refluxed. After 5 hours at reflux the reaction mixture was allowed to cool to room temperature and stirred for 72 hours. The reaction mixture was then poured into 100 mL of iced water and stirred for 20 minutes. This mixture was extracted with CH2Cl2 (3×60 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford the crude product as a green solid. The crude product was purified by flash column chromatography (silica gel, CH2Cl2) to afford 2.21 g (39%) of the product as a yellow solid: mp 133-135° C.; 1H NMR (CDCl3) δ 8.64-8.56 (m, 1H), 8.49-8.39 (m, 1H), 8.10-8.05 (m, 1H), 7.76-7.65 (m, 1H), 7.55-7.47 (m, 1H), 7.36-7.29 (m, 1H), 7.00-6.87 (m, 1H), 3.99 (s, 3H), 3.97 (s, 3H); 13C NMR (CDCl3) δ 192.8, 153.8, 149.4, 147.9, 139.7, 135.2, 129.5, 128.9, 126.2, 125.6, 124.4, 11.8, 110.0, 56.2, 56.1; Anal. Calcd for C15H13NO5. Theoretical: C, 62.72; H, 4.56; N, 4.88. Found: C, 62.74; H, 4.59; N, 4.89.

Workup

  1. customA slight exotherm resulted
  2. temperatureby heating to refluxed
  3. temperatureAfter 5 hours at reflux the reaction mixture
  4. temperatureto cool to room temperature
  5. stirringstirred for 20 minutes
  6. extractionThis mixture was extracted with CH2Cl2 (3×60 mL)
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto afford the crude product as a green solid
  10. customThe crude product was purified by flash column chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-300203cee5c045b8a87ebf89f8b9ce82
Source dataset
uspto-grants-1999_07
Patent number
US05929117

Reaction notes

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