2-Phenylethyl Acetate → 4-Octanoylphenethyl acetate

HRID 862822Notes

Reaction equation

HRID 862822 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:7])[CH3:6].[C:17](Cl)(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]CC>ClC(Cl)C>[C:5]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 76542-Phenylethyl AcetateHCID 66982Decanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 217075284-Octanoylphenethyl acetateYield 40.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Aluminum chloride (111.8 g) was added to dichloroethane (500 ml) in a stream of nitrogen and the mixture was stirred at room temperature. Then, phenethyl acetate (91.8 g) and decanoyl chloride (100 g) were dropwise added thereto under ice-cooling and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20) to give 61.3 g of the subject compound (yield 38%) as an oily substance.

Workup

  1. temperatureunder ice-cooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracted with diethyl ether
  4. washThe ether layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled away
  7. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-d7279e5b6ba940f4853ff27a294eee36
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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