Phenylacetyl chloride → Methyl 5-[4-(Phenylacetyl)phenyl]valerate

HRID 235194Notes

Reaction equation

HRID 235194 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:19]1([CH2:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(=S)=S>[C:19]1([CH2:25][C:26]([C:4]2[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:2][CH:3]=2)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 262942Methyl 5-phenylpentanoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23353739Methyl 5-[4-(Phenylacetyl)phenyl]valerateYield 66%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 5.12 g of methyl 5-phenylvalerate in 25 ml of carbon disulfide, 7.10 g of anhydrous aluminium chloride was added under ice-cooling, and then 4.11 g of phenylacetyl chloride was added dropwise and stirring was continued at room temperature for 6 hours. The reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride layer was washed successively with water, aqueous potassium carbonate solution and water, dried, and then the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1) to afford 5.45 g of colorless crystals. Recrystallization from isopropyl ether gave colorless flakes, mp 53.5°~54° C.

Workup

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride layer was washed successively with water, aqueous potassium carbonate solution and water
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1)

Sources & evidence

ORD record
ord-cf89ed08037e4da49af3bb39c23e54ca
Source dataset
uspto-grants-1997_01
Patent number
US05597848

Reaction notes

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