2,2-Dimethyl-1,3-dioxane-4,6-dione → 7,8-Dihydroxy-3-carboxy-coumarin

HRID 240023

Reaction equation

HRID 240023 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.CC1(C)O[C:18](=[O:19])[CH2:17][C:15](=[O:16])[O:14]1>O>[OH:11][C:8]1[C:9]([OH:10])=[C:2]2[C:3]([CH:4]=[C:17]([C:15]([OH:16])=[O:14])[C:18](=[O:19])[O:1]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 750642,3,4-Trihydroxybenzaldehyde

Product 1

HCID 151737117,8-Dihydroxy-3-carboxy-coumarinYield 74.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

2,3,4-trihydroxybenzaldehyde (106.7 mg, 0.69 mmol) and Meldrum's acid (100 mg, 0.69 mmol) were combined in H2O (1 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 114.1 mg of 7,8-dihydroxy-3-carboxy-coumarin in a 74% yield.

Workup

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

Sources & evidence

ORD record
ord-07911afd4ea7445d99c3f18fb2b5b968
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Linked notes

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