Phenylacetyl chloride → HCID 10709050, compound

HRID 235192Notes

Reaction equation

HRID 235192 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:18]1([CH2:24][C:25](Cl)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(=S)=S>[C:18]1([CH2:24][C:25]([C:4]2[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:2][CH:3]=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 281254Methyl 4-phenylbutyrateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10709050HCID 10709050, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

To a solution of 25.0 g of methyl 4-phenylbutyrate in 100 ml of carbon disulfide, 37.3 g of anhydrous aluminium chloride was added and then a solution of 43.3 g of phenylacetyl chloride in 25 ml of carbon disulfide was added dropwise, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride layer was washed with aqueous potassium carbonate solution, dried, and then the solvent was removed. The residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1→methylene chloride) to afford 27.3 g of colorless crystals. Recrystallization from isopropyl ether gave colorless flakes, mp 54°~54.5° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride layer was washed with aqueous potassium carbonate solution
  3. customdried
  4. customthe solvent was removed
  5. customThe residue was purified by column chromatography on silica gel (methylene chloride:n-hexane=2:1→methylene chloride)

Sources & evidence

ORD record
ord-ffc49b6b7fb547d1ad87a90d1b605821
Source dataset
uspto-grants-1997_01
Patent number
US05597848

Reaction notes

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