Vanillin → (Z)-3-(4-hydroxy-3-methoxyphenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile

HRID 42647

Reaction equation

HRID 42647 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[N:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=1.N1CCCCC1>C(O)C>[OH:9][C:8]1[CH:10]=[CH:11][C:3](/[CH:2]=[C:20](/[C:17]2[CH:18]=[N:19][C:14]([C:13]([F:24])([F:12])[F:23])=[CH:15][CH:16]=2)\[C:21]#[N:22])=[CH:4][C:5]=1[O:6][CH3:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 8082PiperidineHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-

Product 1

HCID 68702729(Z)-3-(4-hydroxy-3-methoxyphenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of vanillin (1.0 g, 6.57 mmol), 2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile (1.222 g, 6.57 mmol) and piperidine (0.71 mL, 7.23 mmol) in absolute ethanol (10 mL) was stirred at reflux for forty-eight hours and then allowed to cool to room temperature. The resulting precipitate was filtered off, washed with water and dried. Recrystallisation from isopropanol afforded (Z)-3-(4-hydroxy-3-methoxyphenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)acrylonitrile as white crystals, 0.904 g (43%).

Workup

  1. temperatureat reflux for forty-eight hours
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with water
  4. customdried
  5. customRecrystallisation from isopropanol

Sources & evidence

ORD record
ord-37b7c793f32b4c61a20e7f3c98835578
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Linked notes

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