4-Chlorophenol → 1-Phenyl-1-(4'-chlorophenoxy)-3,3-dimethyl-butan-2-one

HRID 2071768

Reaction equation

HRID 2071768 reaction equation
Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.[Na]>C(OCC)(=O)C.C(O)C>[C:9]1([CH:2]([O:22][C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 5360545SodiumHCID 134586931-Bromo-3,3-dimethyl-1-phenylbutan-2-one

Product 1

HCID 213260281-Phenyl-1-(4'-chlorophenoxy)-3,3-dimethyl-butan-2-oneYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 25.4 g (0.1 mole) of 1-bromo-1-phenyl-3,3-dimethyl-butan-2-one in 50 ml of ethyl acetate was added dropwise, at the boil, to a solution of 12.85 g (0.1 mole) of 4-chlorophenol and 2.3 g (0.1 mole) of sodium in 100 ml of ethanol. After boiling for 12 hours under reflux, the sodium bromide which had separated out was filtered off hot. The filtrate was distilled in vacuo and the solid residue which remained was recrystallized from ligroin. 20.2 g (67% of theory) of 1-phenyl-1-(4'-chlorophenoxy)-3,3-dimethyl-butan-2-one of melting point 103° C were obtained. pg,48

Workup

  1. temperatureunder reflux
  2. customthe sodium bromide which had separated out
  3. filtrationwas filtered off hot
  4. distillationThe filtrate was distilled in vacuo
  5. customthe solid residue which remained was recrystallized from ligroin

Sources & evidence

ORD record
ord-b4a9457a32c64d9eb987db8ae5af55c0
Source dataset
uspto-grants-1977_09
Patent number
US04048318

Linked notes

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