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

HRID 1386230Notes

Reaction equation

HRID 1386230 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-benzylacetoacetate (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 petroleum 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 petroleum ether (bp. 40-60° C.)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-8c6a08dc6b74496a8542311a0644b118
Source dataset
uspto-grants-2001_07
Patent number
US06265421B1

Reaction notes

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