Piperidine → 2,6-Diisopropyl-4-(2-nitrostyryl)phenol

HRID 53854

Reaction equation

HRID 53854 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])[CH:7]=O)([CH3:3])[CH3:2].[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25]C(O)=O)([O-:18])=[O:17].N1CCCCC1>C1(C)C(C)=CC=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N+:16]([O-:18])=[O:17])[CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 77337(2-Nitrophenyl)acetic acidHCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehyde

Product 1

HCID 537304662,6-Diisopropyl-4-(2-nitrostyryl)phenolYield 87%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 3,5-diisopropyl-4-hydroxybenzaldehyde (0.95 g, 4.6 mmol) and 2-nitrophenyl acetic acid (1.1 g, 6.2 mmol) in xylene (10 ml) was added piperidine (0.05 ml) and the mixture was heated under reflux for 8 hrs while removing water producing with the progress of reaction. After distilling off the solvent followed by purification of the residue by a silica gel column chromatography, recrystallization from hexane gave 2,6-diisopropyl-4-(2-nitrostyryl)phenol (1.3 g, 87%) as crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hrs
  3. customwhile removing water producing
  4. customwith the progress of reaction
  5. distillationAfter distilling off the solvent
  6. customfollowed by purification of the residue by a silica gel column chromatography, recrystallization from hexane

Sources & evidence

ORD record
ord-84581df57dc74116aabc3e0c77082449
Source dataset
uspto-grants-1997_04
Patent number
US05621010

Linked notes

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