Water → 1-[2-Methoxy-4-(2-nitro-vinyl)-phenoxymethyl]-naphthalene

HRID 650979Notes

Reaction equation

HRID 650979 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH:6]=O.C([O-])(=O)C.[NH4+].[N+:28]([CH3:31])([O-:30])=[O:29].O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:31][N+:28]([O-:30])=[O:29])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27166143-Methoxy-4-(naphthalen-1-ylmethoxy)benzaldehyde

Product 1

HCID 538700371-[2-Methoxy-4-(2-nitro-vinyl)-phenoxymethyl]-naphthalene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

36 g of 3-methoxy-4-(naphthalen-1-ylmethoxy)-benzaldehyde, 8.7 9 of ammonium acetate and 10 ml of nitromethane are together heated at reflux for 5 hours in 140 ml of glacial acetic acid. After cooling, the reaction mixture is introduced into 1.5 liters of water. Extraction is carried out twice using 1 liter of ethyl acetate each time. The organic phases are washed 4 once with 500 ml of water and three times using 400 ml of 2N potassium hydrogen carbonate solution each time, dried over magnesium sulfate and concentrated, yielding 1-[2-methoxy-4-(2-nitro-vinyl)-phenoxymethyl]-naphthalene, which can be purified by chromatography on silica gel with ethyl acetate/n-hexane 1:4 and recrystallisation in ethyl acetate/n-hexane, m.p. 120-123° C.

Workup

  1. temperatureAfter cooling
  2. extractionExtraction
  3. washThe organic phases are washed 4 once with 500 ml of water and three times
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9b3fb9908b0c4779b3b6b2031f70eac4
Source dataset
uspto-grants-2001_08
Patent number
US06277849B1

Reaction notes

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