4-Toluenesulfonyl chloride → 1-Tosyloxy-3-(3-methoxyphenyl)propane

HRID 2290936Notes

Reaction equation

HRID 2290936 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[S:19]([O:12][CH2:11][CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 961303-m-Anisyl-1-propanol

Product 1

HCID 5904971-Tosyloxy-3-(3-methoxyphenyl)propaneYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(3-methoxyphenyl)-propanol (69 g, 0.42 mole) and pyridine (400 mL) was stirred at 5° C. as p-toluenesulfonyl chloride (87 g, 0.46 mole) was added portionwise. The reaction mixture was stirred at room temperature for 2 hours, then was poured onto ice/concentrated HCl and was extracted with ether. The extracts were washed with 2N HCl, wawter, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated to yield 126 g yellow oil, (95%); M+ 320.

Workup

  1. additionwas added portionwise
  2. additionwas poured onto ice/concentrated HCl
  3. extractionwas extracted with ether
  4. washThe extracts were washed with 2N HCl, wawter, saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4f25fc0fd6dd493fabbdbd0997ac2a6f
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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