Phenol → HCID 13284250, compound

HRID 2040935Notes

Reaction equation

HRID 2040935 reaction equation
CC([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1Cl)=O.[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:19](=[O:22])([O-])[O-].[K+].[K+].[C:25]([O:29]C)(C)(C)C>[Cu]>[Cl:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:9]=1)[O:29][CH2:25][C:19]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:22]

Participants

6

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 75587Ethanone, 1-(2,5-dichlorophenyl)-

Product 1

HCID 13284250HCID 13284250, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
130 °C

Procedure

A mixture of 307 g (1.62 mol) 2,5-dichloroacetophenone, 193 g (2.05 mol) of phenol, 302 g (2.19 mol) of potassium carbonate and 15 g (0.24 mol) of copper powder was stirred at 130° C. for 10 hours. The reaction mixture was cooled to room temperature, diluted with 500 mL of methyl tert-butyl ether and filtered. The filtered solid was washed with methyl tert-butyl ether and was discarded. The filtrate was washed twice with 500 mL of 1 M aqueous sodium hydroxide. The organic layer was extracted, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was mixed with 350 mL of methanol and stirred at 10° C. for 30 minutes. The resulting suspension was filtered, and the solid was washed with cold methanol, to obtain 236 g of 5-chloro-2-phenoxyacetophenone (compound XV) as an off-white solid. Yield: 58.9%.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtered solid was washed with methyl tert-butyl ether
  4. washThe filtrate was washed twice with 500 mL of 1 M aqueous sodium hydroxide
  5. extractionThe organic layer was extracted
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. additionThe residue was mixed with 350 mL of methanol
  9. stirringstirred at 10° C. for 30 minutes
  10. filtrationThe resulting suspension was filtered
  11. washthe solid was washed with cold methanol

Sources & evidence

ORD record
ord-10d724197a4b467782a88678d24ed65b
Source dataset
uspto-grants-2013_11
Patent number
US08580972B2

Reaction notes

Loading…