4-Toluenesulfonyl chloride → 2,2-Dimethyl-4-(4-p-toluenesulfonyloxybutyl)-1,3-dioxolane

HRID 1577700Notes

Reaction equation

HRID 1577700 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][CH:5]([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:4][O:3]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>[CH3:1][C:2]1([CH3:12])[O:6][CH:5]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2366824-(2,2-Dimethyl-1,3-dioxolan-4-yl)butan-1-ol

Product 1

HCID 127708652,2-Dimethyl-4-(4-p-toluenesulfonyloxybutyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred, ice-cold solution of 6.97 g. of 2,2-dimethyl-4-(4-hydroxybutyl)-1,3-dioxolane [Chem. Abstr., 67, 32617f (1967) ] in 40 ml. of pyridine is added 9.2 g. of p-toluenesulfonyl chloride. The mixture is kept at 0°-5° C. overnight, diluted with ice water, and extracted with ether. The extract is washed successively with water, sodium bicarbonate, water, and brine. The extract is dried over magnesium sulfate and concentrated to give a syrup; pmr (CDCl3) δ 2.50 (singlet).

Workup

  1. extractionextracted with ether
  2. washThe extract is washed successively with water, sodium bicarbonate, water, and brine
  3. dry with materialThe extract is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a syrup

Sources & evidence

ORD record
ord-d13121f045f54e208bc0829fb1ae0e8d
Source dataset
uspto-grants-1981_09
Patent number
US04288632

Reaction notes

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