Ammonium Chloride → 1-(3-Chlorophenyl)-3-(4-chlorophenyl)propan-1-one

HRID 63921Notes

Reaction equation

HRID 63921 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[NH4+].[Cl-]>CO.O.[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 915367571-(3-Chlorophenyl)-3-(4-chlorophenyl)prop-2-en-1-one

Product 1

HCID 247260821-(3-Chlorophenyl)-3-(4-chlorophenyl)propan-1-oneYield 83%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(3-chlorophenyl)-3-(4-chlorophenyl)prop-2-en-1-one (1.38 g, 5 mmol), Zn dust (1.95 g, 30 mmol), NH4Cl (2.67 g, 50 mmol) were combined in MeOH (10 mL) and water (5 mL). The reaction was refluxed for 4 h, cooled to RT then filtered. The filtrate was concentrated to a residue which was purified by chromatography PE/EA (5:1) to give 1-(3-chlorophenyl)-3-(4-chlorophenyl)propan-1-one (1.15 g, 83% yield) as a brown solid. MH+ 279 and TR=2.025 min.

Workup

  1. temperatureThe reaction was refluxed for 4 h
  2. filtrationthen filtered
  3. concentrationThe filtrate was concentrated to a residue which
  4. customwas purified by chromatography PE/EA (5:1)

Sources & evidence

ORD record
ord-2ad4e455ad4d4da5a5d50f6f7b3b6583
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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