Ethanol → 4-Methylumbelliferone

HRID 26696

Reaction equation

HRID 26696 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9]([CH2:12][C:13](OCC)=[O:14])(=O)[CH3:10].C(O)C>S(=O)(=O)(O)O>[CH3:10][C:9]1[C:8]2[C:1](=[CH:3][C:4]([OH:5])=[CH:6][CH:7]=2)[O:2][C:13](=[O:14])[CH:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5054ResorcinolHCID 8868Ethyl Acetoacetate

Product 1

HCID 52805674-MethylumbelliferoneYield 77%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

0.1 mole resorcinol and 0.1 mole ethyl acetylacetate in solution in 100 ml concentrated sulphuric acid are maintained at 5° C. for 3 hours. After recyrstallisation of the solid formed from ethanol, there are obtained 12.5 grams 4-methyl-7-hydroxy-coumarin, melting at 185° C.

Sources & evidence

ORD record
ord-a79709e505384a2687bef6e5cd029a87
Source dataset
uspto-grants-1979_04
Patent number
US04151291

Linked notes

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