Nitroethane → 1-Benzyloxy-2-methoxy-4-(2-nitropropenyl)benzene

HRID 1884261Notes

Reaction equation

HRID 1884261 reaction equation
C(N)CCC.[CH2:6]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=1[O:22][CH3:23])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+:24]([CH2:27][CH3:28])([O-:26])=[O:25]>C(O)(=O)C>[CH2:6]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[C:27]([N+:24]([O-:26])=[O:25])[CH3:28])=[CH:16][C:15]=1[O:22][CH3:23])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 8007ButylamineHCID 755064-(Benzyloxy)-3-methoxybenzaldehyde

Product 1

HCID 534221341-Benzyloxy-2-methoxy-4-(2-nitropropenyl)benzeneYield 18%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.02 g (55.0 mmol) of butylamine was added dropwise to a mixture of 12.1 g (50.0 mmol) of 4-benzyloxy-3-methoxybenzaldehyde, 5.63 g (75.0 mmol) of nitroethane and 120 ml of acetic acid and refluxed for 5 hours by heating. The reaction mixture was cooled and extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=4:1) to give 2.70 g of 1-benzyloxy-2-methoxy-4-(2-nitropropenyl)benzene.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureby heating
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c624cc7d60ae498580f85d1ff21deb2b
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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