4-Hydroxy-6-methyl-2H-1-benzopyran-2-one → HCID 86606247, compound

HRID 131659Notes

Reaction equation

HRID 131659 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[O:5][C:4](=[O:13])[CH:3]=1>C(O)C>[CH2:4]([O:5][CH:6]1[O:1][C:2]2[C:11]3[CH:10]=[C:9]([CH3:12])[CH:8]=[CH:7][C:6]=3[O:5][C:4](=[O:13])[C:3]=2[CH:7]1[C:3]1[C:4](=[O:13])[O:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[CH3:3]

Participants

3

Reactant 1

HCID 546863494-Hydroxy-6-methyl-2H-1-benzopyran-2-one

Product 1

HCID 86606247HCID 86606247, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Hydroxy-6-methylcoumarin (88 mg, 0.5 mmole) was dissolved in ethanol (3 mL). A 40% aqueous gyloxal solution (287 μL, 2.5 mmole) was added and the reaction mixture was refluxed for 3 hours. By cooling to room temperature a white precipitate was precipitated, which was filtered off and washed with ethanol. Obtained was the title compound in a 70% yield and of sufficient purity to be used the next synthesis step:

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customwas precipitated
  3. filtrationwhich was filtered off
  4. washwashed with ethanol
  5. customObtained

Sources & evidence

ORD record
ord-5c64c3dc57cf4e8d99e2b2dff43d6573
Source dataset
uspto-grants-2008_06
Patent number
US07384975B2

Reaction notes

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