3-Chloropropionyl chloride → HCID 69450020, compound

HRID 851955

Reaction equation

HRID 851955 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[O:19][CH3:20]>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][C:4]([C:16]1[CH:15]=[CH:14][C:13]([O:19][CH3:20])=[C:12]([CH3:11])[C:17]=1[CH3:18])=[O:5]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 762692,3-DimethylanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 69450020HCID 69450020, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Chloropropionyl chloride (12.70 g, 100 mmol) is slowly added to a suspension of AlCl3 (16.0 g, 120 mmol) in CH2Cl2 (200 mL) at 0° C. under N2. Next, 2,3-dimethylanisole (13.62 g, 100 mmol) is slowly added at 0° C. The resulting yellow solution is stirred at 0° C. for 30 min, and then quenched by the addition of ice-cold 1.0 N HCl (200 mL) (the first several mL are added very slowly). The resulting mixture is stirred at room temperature for 20 min and then extracted with CH2Cl2. The extract is washed again with water (100 mL) and brine (100 mL), dried over Na2SO4, and concentrated in vacuo to a yield white solid. 1H NMR (CDCl3, 400 MHz): 7.50 (d, J=8.6 Hz, 1H), 6.74 (d, J=8.6 Hz, 1H), 3.90 (t, J=6.8 Hz, 2H), 3.87 (s, 3H), 3.34 (t, J=6.8 Hz, 2H), 2.41 (s, 3H), 2.18 (s, 3H).

Workup

  1. customquenched by the addition of ice-cold 1.0 N HCl (200 mL) (the first several mL
  2. additionare added very slowly)
  3. stirringThe resulting mixture is stirred at room temperature for 20 min
  4. extractionextracted with CH2Cl2
  5. washThe extract is washed again with water (100 mL) and brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo to a yield white solid

Sources & evidence

ORD record
ord-8491993f113647dc85de8d740b553350
Source dataset
uspto-grants-2007_08
Patent number
US07253168B2

Linked notes

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