Hydrochloric Acid → 3-benzyl-5,7-dihydroxy-4-methyl-2H-chromen-2-one

HRID 1862507Notes

Reaction equation

HRID 1862507 reaction equation
O.O.[C:3]1([CH:11]=[C:9]([OH:10])[CH:8]=[C:6]([OH:7])[CH:5]=1)[OH:4].[CH2:12]([CH:19]([C:25]([CH3:27])=O)[C:20](OCC)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(O)C>[CH2:12]([C:19]1[C:20](=[O:21])[O:4][C:3]2[CH:11]=[C:9]([OH:10])[CH:8]=[C:6]([OH:7])[C:5]=2[C:25]=1[CH3:27])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80196Phloroglucinol dihydrateHCID 246929Ethyl alpha-benzylacetoacetate

Product 1

HCID 54285313-benzyl-5,7-dihydroxy-4-methyl-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of phloroglucinol dihydrate (20 g) and ethyl 2-benzylaceto-acetate (27.5 ml) in ethanol (320 ml) was treated with dry HCl at 0° C. for five hours and the solution was kept at that temperature overnight. The yellow solution was concentrated and triturated with water, the solids filtered, washed with water and dried. The resulting hydrate was thrice evaporated to dryness from toluene, triturated with pethroleum ether (bp. 40-60° C.) and filtered. Yield 33.4 g (96%). Melting point 258-260° C.

Workup

  1. customwas kept at that temperature overnight
  2. concentrationThe yellow solution was concentrated
  3. customtriturated with water
  4. filtrationthe solids filtered
  5. washwashed with water
  6. customdried
  7. customevaporated to dryness from toluene
  8. customtriturated with pethroleum ether (bp. 40-60° C.)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-e8dd28d06ad943d18446ba33af4e79a9
Source dataset
uspto-grants-2003_03
Patent number
US06538022B1

Reaction notes

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