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

HRID 240009Notes

Reaction equation

HRID 240009 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.CC1(C)O[C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1>O>[OH:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:3]2[C:2]=1[O:1][C:17](=[O:18])[C:16]([C:14]([OH:15])=[O:13])=[CH:4]2

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 72457168-Hydroxy-3-carboxy-coumarinYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

2,3-dihydroxybenzaldehyde (0.096 g, 0.69 mmol) and Meldrum's acid (0.100 g, 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 0.123 g of 8-hydroxy-3-carboxy-coumarin in an 85% yield: LCMS (ESI) m/z 207 (MH+).

Workup

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

Sources & evidence

ORD record
ord-b313ad17b4cd482691bee4e65b2b0022
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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