Hydrochloric Acid → (E)-1-(2-hydroxy-3-nitrophenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one

HRID 876525Notes

Reaction equation

HRID 876525 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.[OH-].[K+].Cl>CCO>[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])/[CH:12]=[CH:18]/[C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[C:15]([F:14])([F:24])[F:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 2700261-(2-Hydroxy-3-nitrophenyl)-ethanone

Product 1

HCID 58477301(E)-1-(2-hydroxy-3-nitrophenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(2-Hydroxy-3-nitrophenyl)ethanone 1 (788 mg, 4.4 mmol), 2-(trifluoromethyl)benzaldehyde 8 (1.1 g, 6.5 mmol) and 25% aq KOH (90 mL) in EtOH (90 mL) was stirred for 12 h at room temperature. The reaction mixture was poured into ice-water and the pH was adjusted to 2 using conc. HCl. The resulting precipitate was collected by filtration, rinsed with H2O and dried under vacuum to give 9 as a yellow solid (1.4 g, 95% yield).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washrinsed with H2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-26345cc8056941dd99b3f3377d142be3
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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