Resorcinol → 4-Methylumbelliferone

HRID 1602033Notes

Reaction equation

HRID 1602033 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9](OCC)(=[O:14])[CH2:10][C:11]([CH3:13])=O>C1(C)C(C)=CC=CC=1>[OH:2][C:1]1[CH:3]=[C:4]2[C:6]([C:11]([CH3:13])=[CH:10][C:9](=[O:14])[O:5]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5054Resorcinol2×HCID 8868Ethyl Acetoacetate2×

Product 1

HCID 52805674-Methylumbelliferone

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

To a 2 liter flask, a reaction mixture of 55 g (0.5 mole) resorcinol, 71.5 g (1.3 mole) ethyl acetoacetate, 200 g xylene, and 10 g Amberlyst 15 (Rohm and Haas) ion exchange resin catalyst was charged. With heating to a strong reflux at 110-130° C., a Von Pechman condensation reaction was carried out between resorcinol and ethyl acetoacetate to yield 7-hydroxy-4-methyl coumarine product.

Workup

  1. additionwas charged
  2. temperatureWith heating to
  3. customa Von Pechman condensation reaction

Sources & evidence

ORD record
ord-d7f977bbbfe545a98187dcce70a1718e
Source dataset
uspto-grants-1999_11
Patent number
US05980593

Reaction notes

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