Hydrochloric Acid → 7-Hydroxy-3-(4-hydroxyphenyl)-4-methylcoumarin

HRID 1058982Notes

Reaction equation

HRID 1058982 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12](=[O:26])[O:13][C:14]3[C:19]([C:20]=2[CH3:21])=[CH:18][CH:17]=[C:16]([O:22]C(=O)C)[CH:15]=3)=[CH:7][CH:6]=1)(=O)C.Cl>C1COCC1.[OH-].[Na+]>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12](=[O:26])[O:13][C:14]3[C:19]([C:20]=2[CH3:21])=[CH:18][CH:17]=[C:16]([OH:22])[CH:15]=3)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18669495HCID 18669495, compound

Product 1

HCID 102210247-Hydroxy-3-(4-hydroxyphenyl)-4-methylcoumarinYield 36.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 3-(4-acetoxyphenyl)-7-acetoxy-4-methylcoumarin (500 mg) in THF (10 mL) and 1N aqueous sodium hydroxide (10 mL) was stirred for 1 h. The mixture is acidified to pH=1 with concentrated HCl and extracted with EtOAc 1 water. The organic layer was washed with brine and dried over MgSO4. Evaporation of the solvent and trituration of the residue with ether gave the title compound (140 mg)

Workup

  1. extractionextracted with EtOAc 1 water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customEvaporation of the solvent and trituration of the residue with ether

Sources & evidence

ORD record
ord-cc97984b9cc8440c983030076e7e2aa4
Source dataset
uspto-grants-2003_02
Patent number
US06518301B1

Reaction notes

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