Piperidine → Ethyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)-2-(3-pyridyl)propenoate

HRID 1193966Notes

Reaction equation

HRID 1193966 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]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:19]=1.N1CCCCC1>C(O)C>[C:14]([C:11]1[CH:10]=[C:7]([CH:8]=[C:24]([C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:12]=1[OH:13])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 96490Ethyl 3-pyridylacetate

Product 1

HCID 54533232Ethyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)-2-(3-pyridyl)propenoateYield 46.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Here, 3,5-di-t-butyl-4-hydroxybenzaldehyde (223 g, 0.952 mol), Ethyl 3-pyridylacetate (157.2 g, 0.952 mol), piperidine (81 g, 0.952 mol) and p-tolunesulfonic acid (0.5 g) are combined in ethanol (2,400 ml) and heated at reflux for 48 hours. The reaction mixture is allowed to cool to room temperature and then stirred on an ice bath, whereupon the product begins to crystallize. The mixture is stored in the freezer overnight, filtered and rinsed with cold ethanol-water (1:1). The product is dried, giving ethyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)-2-(3-pyridyl)propenoate (169.1 g) Mp 119.5°-120.5° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. customto crystallize
  4. customis stored in the freezer overnight
  5. filtrationfiltered
  6. washrinsed with cold ethanol-water (1:1)
  7. customThe product is dried

Sources & evidence

ORD record
ord-766fb633e6d849bb8414aa589ab96adf
Source dataset
uspto-grants-1989_03
Patent number
US04812460

Reaction notes

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