P-Chloroacetophenone → (E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 33450

Reaction equation

HRID 33450 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(O[CH:15](OC(C)C)[N:16]([CH3:18])[CH3:17])(C)C>>[CH3:15][N:16]([CH3:18])/[CH:17]=[CH:9]/[C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:10]

Participants

3

Reactant 2

HCID 7467P-ChloroacetophenoneHCID 87682N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine

Product 1

HCID 5375260(E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-oneYield 99%

Procedure

A solution of 1-(4-chlorophenyl)ethane-1-one (35.0 g, 226 mmol) and N,N Dimethylformamide diisopropylacetal (35 mL) was heated to reflux for 16 hours. The reaction mixture was cooled to room temperature and treated with hexanes (50 mL). The resulting solid was collected via filtration and washed with hexanes to provide the title compound as a yellow solid (47.12 g, 99% yield): HPLC Retention Time; 6.45 min (Method B). M+1; 209.

Workup

  1. temperatureto reflux for 16 hours
  2. filtrationThe resulting solid was collected via filtration
  3. washwashed with hexanes

Sources & evidence

ORD record
ord-7b143d0fd7a04fcfb5f097754da81e17
Source dataset
uspto-grants-2008_09
Patent number
US07429599B2

Linked notes

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