Resorcinol → 7-Hydroxy-4-phenylcoumarin

HRID 21571

Reaction equation

HRID 21571 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9]([CH2:17][C:18](OCC)=[O:19])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>OP(O)(O)=O>[OH:2][C:1]1[CH:3]=[C:4]2[C:6]([C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:17][C:18](=[O:19])[O:5]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5054ResorcinolHCID 7170Ethyl benzoylacetate

Product 1

HCID 53574797-Hydroxy-4-phenylcoumarin

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of resorcinol (20 g), ethyl benzoylacetate (23.8 mL) and O-phosphoric acid (130 mL) was heated at 85° C. (care!) for 1 hr. The solution was cooled, poured onto H2O, extracted 3×EtOAc/THF, washed twice with H2O, and then twice with brine. The organic phase was dried and evaporated. Trituration with Et2O followed by filtration afforded the title compound as a solid.

Workup

  1. temperatureThe solution was cooled
  2. additionpoured onto H2O
  3. extractionextracted 3×EtOAc/THF
  4. washwashed twice with H2O
  5. customThe organic phase was dried
  6. customevaporated
  7. filtrationTrituration with Et2O followed by filtration

Sources & evidence

ORD record
ord-676f55a760bb46bcbae02c9496dfc607
Source dataset
uspto-grants-1995_06
Patent number
US05424320

Linked notes

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