Benzene → Methyl 4-[(1Z)-2-nitropenta-1-enyl]benzoate

HRID 351348

Reaction equation

HRID 351348 reaction equation
C(N)CCC.[CH:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)=O.C1C=CC=CC=1.[N+:24]([CH2:27][CH2:28][CH2:29][CH3:30])([O-:26])=[O:25]>C(O)(=O)C.O>[N+:24](/[C:27](/[CH2:28][CH2:29][CH3:30])=[CH:6]\[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)([O-:26])=[O:25]

Participants

7

Reactant 4

HCID 241BenzeneHCID 8007ButylamineHCID 123021-NitrobutaneHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 58807290Methyl 4-[(1Z)-2-nitropenta-1-enyl]benzoateYield 46.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

n-Butylamine (8.31 ml, 84.1 mmol) and methyl 4-formylbenzoate (10.6 g, 64.7 mmol) was heated with reflux benzene (50 ml) in a Dean-Stark trap until a theoretical amount of water was recovered. The solvent was evaporated under reduced pressure. To the residue were added glacial acetic acid (30 ml) and nitrobutane (10.0 g, 97.0 mmol), and the mixture was stirred at 110° C. for 4 hrs. and allowed to cool to room temperature. The insoluble materials were filtered off and dried to give the title compound (7.53 g) as a pale-yellow powder.

Workup

  1. customwas recovered
  2. customThe solvent was evaporated under reduced pressure
  3. temperatureto cool to room temperature
  4. filtrationThe insoluble materials were filtered off
  5. customdried

Sources & evidence

ORD record
ord-55c2bf59c9ae48ebafa26b9b38aadab3
Source dataset
uspto-grants-2007_02
Patent number
US07183415B2

Linked notes

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