Water → HCID 10798396, compound

HRID 1383425Notes

Reaction equation

HRID 1383425 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].[F:10][CH:11]([C:17]([CH3:19])=O)[C:12](OCC)=[O:13].S(=O)(=O)(O)O.O>O1CCOCC1>[F:10][C:11]1[C:12](=[O:13])[O:4][C:3]2[C:5]([C:17]=1[CH3:19])=[CH:6][CH:7]=[C:8]([OH:9])[C:2]=2[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 118432-MethylresorcinolHCID 230078Ethyl 2-fluoroacetoacetate

Product 1

HCID 10798396HCID 10798396, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-methylresorcinol (3.23 g, 26.02 mmoles), ethyl 2-fluoro-acetoacetate [E. B. Banks, N. J. Lawrence, A. L. Popplewell, J. Chem. Soc., Chem. Commun, 343 (1994)] (3.85 g, 25.99 mmoles) in 0.5 mL of 1,4-dioxane was added dropwise, at 0° C. and under an inert atmosphere, to 25 mL of concentrated sulfuric acid. The reaction mixture was stirred for 1.5 hours, while the temperature was increased to 25° C. Cold water (100 mL) was added, the reaction mixture was stirred for 15 minutes and the resulting precipitate was collected by suction filtration, dried in vacuo, affording 4.56 g (84% yield) of 3-fluoro-4,8-dimethyl-7-hydroxycoumarin as a white solid. An analytical sample was obtained by recrystallisation from methanol:water: mp 260° C. (decomp.).

Workup

  1. stirringthe reaction mixture was stirred for 15 minutes
  2. filtrationthe resulting precipitate was collected by suction filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1125ceca5232464ea93a9760a784e9a4
Source dataset
uspto-grants-2001_07
Patent number
US06255324B1

Reaction notes

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