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

HRID 240028

Reaction equation

HRID 240028 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:7]([CH:8]=O)[C:6]([OH:11])=[CH:5][CH:4]=1.CC1(C)O[C:18](=[O:19])[CH2:17][C:15](=[O:16])[O:14]1>O>[CH3:1][O:2][C:3]1[CH:10]=[C:7]2[C:6](=[CH:5][CH:4]=1)[O:11][C:18](=[O:19])[C:17]([C:15]([OH:16])=[O:14])=[CH:8]2

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 7117176-methoxy-2-oxo-2H-chromene-3-carboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

5-methoxy-salicylaldehyde (211.1 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 241.1 mg of 6-methoxy-3-carboxy-coumarin in a 79% yield.

Workup

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

Sources & evidence

ORD record
ord-1bfe4d034d2041869f9065faca74f02e
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Linked notes

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