Nitromethane → HCID 86653766, compound

HRID 1528115Notes

Reaction equation

HRID 1528115 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][CH3:14])=[C:7]([CH3:15])[C:4]=1[CH:5]=O.C([O-])(=O)C.[NH4+].[N+:21]([CH3:24])([O-:23])=[O:22]>>[CH3:1][O:2][C:3]1[C:4]([CH:5]=[CH:24][N+:21]([O-:23])=[O:22])=[C:7]([CH3:15])[C:8]([O:13][CH3:14])=[C:9]([CH3:12])[C:10]=1[CH3:11]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27526052,5-Dimethoxy-3,4,6-trimethylbenzaldehyde

Product 1

HCID 86653766HCID 86653766, compound

Conditions

Temperature
80 °C

Procedure

In a 500 mL round bottom flask was placed 2,5-dimethoxy-3,4,6-trimethylbenzaldehyde (2.5 g, 12 mmol) and ammonium acetate (1.3 g, 17 mmol). The solids were taken up in nitromethane (240 mL), and the mixture warmed to 80° C. for 90 min. After the reaction was complete, volatiles were removed in vacuo, the residue was dissolved in ethyl acetate (200 mL), washed with water and brine (50 mL each), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 3.3 g 1,4-dimethoxy-2,3,5-trimethyl-6-(2-nitrovinyl)benzene as a yellow solid. Further purification was performed by digesting the solid product in cyclohexane for 3 hrs, after which the 2.5 g pure compound 1,4-dimethoxy-2,3,5-trimethyl-6-(2-nitrovinyl)benzene was obtained. 1H NMR (CDCl3, 400 MHz) 8.24 (d, 1H), 7.95 (d, 1H), 3.65 (s, 3H), 3.63 (s, 3H), 2.41 (s, 3H), 2.25 (s, 3H), 2.21 (s, 3H) ppm.

Workup

  1. customIn a 500 mL round bottom flask was placed
  2. customvolatiles were removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  4. washwashed with water and brine (50 mL each)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3848016b0d245bd8b4d88edb85a7d28
Source dataset
uspto-grants-2015_07
Patent number
US09090576B2

Reaction notes

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