Pyridine → 2-(4-Octanoyl phenyl)ethyl p-toluene sulfonate

HRID 1595062Notes

Reaction equation

HRID 1595062 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.N1C=CC=CC=1>ClCCl>[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([O:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 222186582-(4-Octanoylphenyl)ethanol

Product 1

HCID 110477072-(4-Octanoyl phenyl)ethyl p-toluene sulfonateYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4′-(2-Hydroxy ethyl)octanophenone (1.0 g) prepared in the step B was dissolved in dichloromethane (10 ml) to obtain a solution. p-Toluene sulfonyl chloride (923 mg) and pyridine (383 mg) were added to the solution with cooling, and the mixture was stirred at room temperature for 2 hours. After the reaction, ice water was added to the solution, the solution was stirred at room temperature for 20 minutes. Dichloromethane layer was washed with 2% hydrochloric acid, sodium bicarbonate solution, and water. The dichloromethane layer was dried over anhydrous sodium sulfate, and concentrated. The residue was recrystallized from hexane-ethyl acetate (10:1) to obtain 2-(4-octanoyl phenyl)ethyl p-toluene sulfonate (950 mg) in the form of colorless crystal.

Workup

  1. customto obtain a solution
  2. temperaturewith cooling
  3. additionwas added to the solution
  4. stirringthe solution was stirred at room temperature for 20 minutes
  5. washDichloromethane layer was washed with 2% hydrochloric acid, sodium bicarbonate solution, and water
  6. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-9b4972b9135a43ea94e7b2596949e09d
Source dataset
uspto-grants-2001_09
Patent number
US06284915B1

Reaction notes

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