4-Methoxyphenylacetyl chloride → 2-(4-Methoxyphenyl)-1-phenylethan-1-one

HRID 1955787Notes

Reaction equation

HRID 1955787 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](Cl)=[O:11])=[CH:5][CH:4]=1>C1C=CC=CC=1>[C:3]1([C:10](=[O:11])[CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 27346884-Methoxyphenylacetyl chloride

Product 1

HCID 2310922-(4-Methoxyphenyl)-1-phenylethan-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-Phenyl-2-(4-methoxyphenyl)ethanone was prepared from benzene and 4-methoxyphenylacetyl chloride (prepared by heating the commercially available carboxylic acid in thionyl chloride and subsequent concentration) using the method described in step A of Example 9. 1-Phenyl-2-(4-methoxyphenyl)ethanone was converted to the title compound following the procedures outlined in steps C-E of Example 1, except for the following modifications: 1) in step C, the acidic hydrolysis reaction, after dilution with H2O, was extracted 2× with Et2O prior to basification, extraction 3× with EtOAc and isolation of the desired amine after concentration; 2) the prep HPLC purification of step D was omitted; and 3) in step E, the final product was purified by prep HPLC using 46% solvent B as eluant.

Workup

  1. customprepared
  2. temperatureby heating
  3. concentrationthe commercially available carboxylic acid in thionyl chloride and subsequent concentration)
  4. custom1) in step C, the acidic hydrolysis reaction
  5. extractionafter dilution with H2O, was extracted 2× with Et2O
  6. extractionto basification, extraction 3× with EtOAc and isolation of the desired amine
  7. concentrationafter concentration
  8. custom2) the prep HPLC purification of step D
  9. customand 3) in step E, the final product was purified by prep HPLC

Sources & evidence

ORD record
ord-370b0de3427b4fc49c44bbd6e32d9f46
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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