Aluminum(III) Chloride → 3-Acetamido-6-acetoxy-3-[2-(4-octanoylphenyl)ethyl]hexyl acetate

HRID 842259Notes

Reaction equation

HRID 842259 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([O:8][CH2:9][CH2:10][C:11]([NH:27][C:28](=[O:30])[CH3:29])([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])(=[O:7])[CH3:6]>ClCCCl.C(Cl)(=O)CCCCCCC>[C:5]([O:8][CH2:9][CH2:10][C:11]([NH:27][C:28](=[O:30])[CH3:29])([CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:9](=[O:8])[CH2:10][CH2:11][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:25][CH:26]=1)[CH2:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 6451240Aluminum(III) Chloride2×HCID 226187933-Acetamido-6-acetoxy-3-(2-phenylethyl)hexyl acetate

Product 1

HCID 226186813-Acetamido-6-acetoxy-3-[2-(4-octanoylphenyl)ethyl]hexyl acetateYield 148.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8124Octanoyl chlorideSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of anhydrous aluminum chloride (1.4 g) in 1,2-dichloroetane (20 ml), octanoyl chloride was carefully added at room temperature and the suspension was stirred until anhydrous aluminum chloride was entirely dissolved. To the reaction solution, a solution of 3-acetamido-6-acetoxy-3-(2-phenylethyl)hexyl acetate (780 mg) in 1,2-dichloroethane (10 ml) was dropwise added at room temperature over 10 minutes. The reaction temperature raised to 70° C. and the mixture was stirred for 30 minutes. After cooling, the reaction solution was poured into ice-water and extracted with chloroform. The chloroform layer was washed with water and a saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled away. The residue obtained was purified by silica gel chromatography (eluent; hexane-ethyl acetate=1:1) to give the subject compound (780 mg) as a yellowish oily substance.

Workup

  1. additionwas carefully added at room temperature
  2. dissolutionwas entirely dissolved
  3. temperatureAfter cooling
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materiala saturated brine, dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled away
  8. customThe residue obtained
  9. customwas purified by silica gel chromatography (eluent; hexane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8a532fcf448648c6afa804f30ca8c39d
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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