Hydrochloric Acid → (E)-2-hydroxy-3-(3-(3-(trifluoromethyl)phenyl)acryloyl)benzoic acid

HRID 876536Notes

Reaction equation

HRID 876536 reaction equation
[C:1]([C:4]1[C:5]([OH:13])=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=O.[OH-].[K+].Cl>C(O)C>[OH:13][C:5]1[C:4]([C:1](=[O:3])/[CH:2]=[CH:19]/[C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([C:15]([F:14])([F:24])[F:25])[CH:17]=2)=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 679903-(Trifluoromethyl)benzaldehydeHCID 108992643-acetyl-2-hydroxybenzoic acid

Product 1

HCID 58477338(E)-2-hydroxy-3-(3-(3-(trifluoromethyl)phenyl)acryloyl)benzoic acidYield 47.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-acetyl-2-hydroxybenzoic acid 32 (0.9 g, 5 mmol) and 3-(trifluoromethyl)benzaldehyde 33 (0.96 g, 5.5 mmol) were dissolved in 100 mL ethanol. After addition of the same volume of 25% aq KOH, the reaction mixture was stirred for 24 h. The mixture was poured into ice-water and the PH was adjusted to 2 with conc. HCl. The precipitate was filtered, washed with H2O and dried to give 34 (0.8 g, 47% yield)

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with H2O
  3. customdried

Sources & evidence

ORD record
ord-6077cd69595b4a3db9d77bc0a7c44c2b
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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