Hexane → 2,6-Di-tert-butyl-4-(2-nitrostyryl)phenol

HRID 53852

Reaction equation

HRID 53852 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]C(O)=O)([O-:20])=[O:19].N1CCCCC1.CCCCCC>C1(C)C(C)=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N+:18]([O-:20])=[O:19])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8082PiperidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 541417492,6-Di-tert-butyl-4-(2-nitrostyryl)phenolYield 62.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (8.09 g, 34.5 mmol) and 2-nitrophenylacetic acid (9.40 g, 51.9 mmol) in xylene (60 ml) was added piperidine (0.3 ml) and the mixture was heated under reflux for 26 hrs while removing water producing with the progress of reaction. After allowing to stand overnight, hexane was added to afford as crystals 2,6-di-tert-butyl-4-(2-nitrostyryl)phenol (7.67 g, 62.9%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 26 hrs
  3. customwhile removing water producing
  4. customwith the progress of reaction

Sources & evidence

ORD record
ord-3925ace3a9be4734b0ae067507043c4f
Source dataset
uspto-grants-1997_04
Patent number
US05621010

Linked notes

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