(4-Nitrophenyl)acetic acid → HCID 67769581, compound

HRID 1720072Notes

Reaction equation

HRID 1720072 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][O:15]C1C=CC(C=O)=CC=1.N1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[CH2:30](Cl)Cl>>[CH3:14][O:15][C:4]1([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]([CH:10]=[CH:11][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:8][CH2:9]1

Participants

5

Reactant 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 6344DichloromethaneHCID 8082PiperidineHCID 312444-Methoxybenzaldehyde

Product 1

HCID 67769581HCID 67769581, compoundYield 45.5%

Procedure

A suspension of p-nitrophenylacetic acid (9.05 g, 50 mmol), 4-methoxybenzaldehyde (7.5 g, 55.1 mmol), and piperidine (2.5 ml) was heated at reflux for 45 min. After allowing to cool to room temperature, the reaction mixture was dissolved in CH2Cl2 (100 ml), washed with 0.1N NaOH (2×20 ml), and dried (MgSO4). The solvent was removed under reduced pressure to provide a solid which was recrystallized from EtOH to give 5.8 g (45.5%) of 4-methoxy-4-nitrostilbene as orange-colored crystals, mp 131°-132° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 min
  3. washwashed with 0.1N NaOH (2×20 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed under reduced pressure
  6. customto provide a solid which
  7. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-f18ba55298164585bccee317d9cf8633
Source dataset
uspto-grants-1996_04
Patent number
US05504101

Reaction notes

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