2,2-Dimethyl-1,3-dioxane-4,6-dione → 6-(Trifluoromethoxy)-2-oxo-2H-chromene-3-carboxylic acid

HRID 240034

Reaction equation

HRID 240034 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:11]=[C:8]([CH:9]=O)[C:7]([OH:12])=[CH:6][CH:5]=1.CC1(C)O[C:21](=[O:22])[CH2:20][C:18](=[O:19])[O:17]1>O>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:11]=[C:8]2[C:7](=[CH:6][CH:5]=1)[O:12][C:21](=[O:22])[C:20]([C:18]([OH:19])=[O:17])=[CH:9]2

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehyde

Product 1

HCID 100618686-(Trifluoromethoxy)-2-oxo-2H-chromene-3-carboxylic acidYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

5-trifluoromethoxy-salicylaldehyde (286.0 mg, 1.39 mmol) and Meldrum's acid (200 mg, 1.39 mmol) were combined in H2O (2 mL). The solution was stirred at 75° C. for 2 h. After cooling to room temperature, the precipitate was filtered and dried at suction to give 189.1 mg of 6-trifluoromethoxy-3-carboxy-coumarin in a 50% yield.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered
  3. customdried at suction

Sources & evidence

ORD record
ord-75c7661c2c424a7abc926de33611af6d
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Linked notes

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