2,2-Dimethyl-1,3-dioxane-4,6-dione → 6,7-Dihydroxycoumarin-3-carboxylic Acid

HRID 240030Notes

Reaction equation

HRID 240030 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:8][C:9]=1[OH:10])[CH:6]=O.CC1(C)O[C:18](=[O:19])[CH2:17][C:15](=[O:16])[O:14]1>O>[OH:10][C:9]1[CH:8]=[C:5]2[C:4](=[CH:3][C:2]=1[OH:1])[O:11][C:18](=[O:19])[C:17]([C:15]([OH:16])=[O:14])=[CH:6]2

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 6433872,4,5-Trihydroxybenzaldehyde

Product 1

HCID 139895536,7-Dihydroxycoumarin-3-carboxylic AcidYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

4,5-dihydroxy-salicylaldehyde (213.0 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 271.0 mg of 6,7-dihydroxy-3-carboxy-coumarin in an 88% yield.

Workup

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

Sources & evidence

ORD record
ord-4da350373d674a1b97ba045fcabf4484
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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