Sulfuric Acid → 7-Hydroxy-4-phenylcoumarin

HRID 2116653Notes

Reaction equation

HRID 2116653 reaction equation
OS(O)(=O)=O.[C:6]1([CH:13]=[CH:12][CH:11]=[C:9]([OH:10])[CH:8]=1)[OH:7].[C:14]([CH2:22][C:23](OCC)=[O:24])(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[OH:7][C:6]1[CH:8]=[C:9]2[C:11]([C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:22][C:23](=[O:24])[O:10]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 5054ResorcinolHCID 7170Ethyl benzoylacetate

Product 1

HCID 53574797-Hydroxy-4-phenylcoumarinYield 96.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated H2SO4 (65 ml) was added to a mixture of resorcinol (26.7 g, 242.4 mmol) and ethyl benzoylacetate (51.26 g, 266.7 mmol) at 0° C. The resulting suspension was stirred for 24 h at room temperature. Water (2 L) was added and the mixture was stirred for 1 h. The solid was filtered, washed with water (2 L) and dried to give 55.78 g of the titled compound.

Workup

  1. stirringthe mixture was stirred for 1 h
  2. filtrationThe solid was filtered
  3. washwashed with water (2 L)
  4. customdried

Sources & evidence

ORD record
ord-d0c1afa3cbea499185a855f3e0e5d47e
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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