Hydrochloric Acid → 3-(4-Chlorobenzyl)-5,7-dihydroxy-4-methyl-2H-1-benzopyran-2-one

HRID 1835683Notes

Reaction equation

HRID 1835683 reaction equation
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[Cl:10][C:11]1[CH:26]=[CH:25][C:14]([CH2:15][CH:16]([C:22]([CH3:24])=O)[C:17](OCC)=[O:18])=[CH:13][CH:12]=1.Cl>C(O)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][C:16]2[C:17](=[O:18])[O:2][C:1]3[CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[C:3]=3[C:22]=2[CH3:24])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 359PhloroglucinolHCID 2757404Ethyl 2-(4-chlorobenzyl)acetoacetate

Product 1

HCID 235003553-(4-Chlorobenzyl)-5,7-dihydroxy-4-methyl-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of phloroglucinol (1.57 g) and ethyl 2-(4-chlorobenzyl)-acetoacetate (3.18 g) in ethanol (25 ml) was treated with dry HCl at 0° C. for 1.5 hours and the solution was kept at that temperature overnight. Solvent was evaporated and the precipitate triturated with water. Yield 3.87 g (98%). Melting point 270-278° C.

Workup

  1. customwas kept at that temperature overnight
  2. customSolvent was evaporated
  3. customthe precipitate triturated with water

Sources & evidence

ORD record
ord-d44aa24134a64430bc1eff22129eeb62
Source dataset
uspto-grants-2004_08
Patent number
US06774103B1

Reaction notes

Loading…