Hydrochloric Acid → 1-(4-Methoxyphenyl)-2-phenylethan-1-one

HRID 2372361Notes

Reaction equation

HRID 2372361 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:15]1([O:21][CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>C(Cl)Cl>[CH3:22][O:21][C:15]1[CH:20]=[CH:19][C:18]([C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 7679Phenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2310931-(4-Methoxyphenyl)-2-phenylethan-1-oneYield 63.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Phenylacetyl chloride (30.9 g, 0.2 mol) in CH2Cl2 (100 ml) was added dropwise to a solution of AlCl3 (32 g, 0.24 mol) and anisole (21.6 g, 0.2 mol) in CH2Cl2 (400 ml) at room temperature. The reaction was complete (by TLC) after 4 hours and was poured over an ice; 10% HCl slurry. The organic layer was washed with H2O and brine, dried over MgSO4, and the solvent was removed under reduced pressure. The crude solid was chromatographed SiO2 (1500 g), eluting with toluene to afford 11 (20.2 g, 63.7%, para isomer), m.p. 74°-75.5° C.

Workup

  1. customafter 4 hours
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customThe crude solid was chromatographed SiO2 (1500 g)
  6. washeluting with toluene

Sources & evidence

ORD record
ord-c11cbb71094546d4b7d71c19b0261116
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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