4-Toluenesulfonyl chloride → 2-(4-Methylphenyl)ethyl 4-methylbenzene-1-sulfonate

HRID 1838919Notes

Reaction equation

HRID 1838919 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][OH:9])=[CH:3][CH:2]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)([O:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 952944-Methylphenethyl alcohol

Product 1

HCID 2853862-(4-Methylphenyl)ethyl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2.8 ml of 2-p-tolylethanol are introduced into 40 ml of pyridine with ice-bath cooling, treated with 4.96 g of p-toluenesulphonyl chloride, and stirred at 0° C. for 30 minutes and at room temperature for 2 hours. The reaction mixture is then slowly stirred into about 150 g of ice/water. The precipitated product is filtered off with suction, washed a number of times with water, dissolved in methylene chloride, dried over magnesium sulphate and concentrated in vacuo. 5.8 g of 2-p-tolylethyl tosylate are obtained, which is employed in the next stage without further purification.

Workup

  1. temperaturecooling
  2. filtrationThe precipitated product is filtered off with suction
  3. washwashed a number of times with water
  4. dissolutiondissolved in methylene chloride
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55d711dacf6a4a8abe91fef7cd241cef
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

Loading…