(4-Nitrophenyl)acetic acid → 4-[2-(3,4-Dichlorophenyl)ethenyl]nitrobenzene

HRID 488482Notes

Reaction equation

HRID 488482 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].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Cl:23])C=O>N1CCCCC1>[Cl:14][C:15]1[CH:16]=[CH:17][C:20]([CH:11]=[CH:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:21][C:22]=1[Cl:23]

Participants

4

Reactant 2

HCID 4661(4-Nitrophenyl)acetic acidHCID 227103,4-Dichlorobenzaldehyde

Product 1

HCID 540912824-[2-(3,4-Dichlorophenyl)ethenyl]nitrobenzeneYield 27.5%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of p-nitrophenylacetic acid (51.23 g, 0.28 mol) and 3,4-dichlorobenzaldehyde (49.50 g, 0.28 mol) in piperidine (50 mL) was heated to 150-160° C. for 5 hours under a N2 atmosphere. After cooling the reaction mixture, the precipitate was triturated in boiling methanol (MeOH) (50 mL) and then cooled to −5° C. for 12 hours. The crystalline precipitate was filtered off, rinsed with cold MeOH and dried at room temperature in a vacuum oven overnight to yield an orange solid, 22.71 g (0.077 mol, 27%) of the desired product.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customthe precipitate was triturated
  3. temperaturecooled to −5° C. for 12 hours
  4. filtrationThe crystalline precipitate was filtered off
  5. washrinsed with cold MeOH
  6. customdried at room temperature in a vacuum oven overnight

Sources & evidence

ORD record
ord-9f35c529add648a68d2e2416f91a50d1
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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