Hydrochloric Acid → 4-[5-(4-Chlorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

HRID 537678Notes

Reaction equation

HRID 537678 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH3:21])=[C:6]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])[CH:7]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>CS(C)=O.[Cu]I>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:2]2[CH:3]=[CH:4][C:5]([CH2:20][CH3:21])=[C:6]([CH:8]3[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]3=[O:19])[CH:7]=2)=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 46844-ChlorophenolHCID 62657Potassium Phosphate, TribasicHCID 666785694-(5-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

Product 1

HCID 666796524-[5-(4-Chlorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-(5-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (200 mg, 0.57 mmol), 4-chlorophenol (110 mg, 0.86 mmol), copper(I) iodide (109 mg, 0.57 mmol), 1,10-phenanthroline (103 mg, 0.57 mmol) and potassium phosphate (483 mg, 2.28 mmol), in dimethylsulfoxide (3.5 ml) is heated to 200° C. under microwave irradiation for 30 minutes. The mixture is cooled to room temperature, poured into 2M aqueous hydrochloric acid and extracted with dichloromethane. The organic extract is washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The solvent is evaporated under reduced pressure and the residue is purified by column chromatography on silica gel to give 4-[5-(4-chlorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washis washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe solvent is evaporated under reduced pressure
  8. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a96a34d8aa6743f3b77267c36c7d61db
Source dataset
uspto-grants-2014_10
Patent number
US08865623B2

Reaction notes

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