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

HRID 1577711Notes

Reaction equation

HRID 1577711 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. Absrtr., 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-2463bb0b6e704557bbfd811dcf4cb1cc
Source dataset
uspto-grants-1981_09
Patent number
US04288630

Reaction notes

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