Dimethyl Sulfoxide → 4-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxylic acid

HRID 876537Notes

Reaction equation

HRID 876537 reaction equation
[OH:1][C:2]1[C:10]([C:11](=[O:24])/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CS(C)=O>O1CCOCC1>[O:24]=[C:11]1[C:10]2[C:2](=[C:3]([C:4]([OH:6])=[O:5])[CH:7]=[CH:8][CH:9]=2)[O:1][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)=[CH:12]1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 58477338(E)-2-hydroxy-3-(3-(3-(trifluoromethyl)phenyl)acryloyl)benzoic acid

Product 1

HCID 584772184-oxo-2-(3-(trifluoromethyl)phenyl)-4H-chromene-8-carboxylic acidYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (E)-2-hydroxy-3-(3-(3-(trifluoromethyl)phenyl)acryloyl)benzoic acid 34 (0.8 g, 2.4 mmol), SeO2 (0.79 g, 7.1 mmol) and DMSO (5 mL) in dioxane (150 mL) was heated at reflux for 1 h. The black solid was filtered and the dioxane was evaporated. The remaining oil was suspended in H2O, filtered and dried to give 35 (0.56 g, 76% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. filtrationThe black solid was filtered
  4. customthe dioxane was evaporated
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-bc9c75ab989f42129c4640c7859cfc25
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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