Phenylacetyl chloride → Ethyl 3-[4-(phenylacetyl)phenyl]propionate

HRID 1937772Notes

Reaction equation

HRID 1937772 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:15]1([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+]>ClCCCl>[C:1]1([CH2:7][C:8]([C:18]2[CH:19]=[CH:20][C:15]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][CH:17]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 16237Ethyl 3-phenylpropionateHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22461793Ethyl 3-[4-(phenylacetyl)phenyl]propionate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Phenylacetyl chloride (3.4 ml) is added to a solution of anhydrous aluminum chloride (4.27 g) in 1,2-dichloroethane (35 ml) under ice cooling, and then a solution of ethyl 3-phenylpropionate (5.1 g) in anhydrous 1,2-dichloroethane (5 ml) is added dropwise thereto. The mixture is stirred under ice cooling for 20 minutes and at room temperature overnight. The reaction mixture is added little by little to a saturated aqueous sodium hydrogencarbonate solution (150 ml) containing ice (100 g). The resulting precipitates are filtered out. Ether is added to the filtrate. The organic layer is washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give ethyl 3-[4-(phenylacetyl)phenyl]propionate as crystals.

Workup

  1. customThe resulting precipitates
  2. filtrationare filtered out
  3. additionEther is added to the filtrate
  4. washThe organic layer is washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-afc4decd1254461d821db49b343cc648
Source dataset
uspto-grants-2002_05
Patent number
US06395932B1

Reaction notes

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