Water → 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

HRID 1982239Notes

Reaction equation

HRID 1982239 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.O>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 7528Solketal

Product 1

HCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolane (26 g, 0.2 mol) is added to 38 g of p-toluenesulfonyl chloride (0.2 mol) in 200 ml of pyridine and allowed to stand at 0° C. for 24 h. Water was added, and the mixture extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine, dried over Na2SO4, and evaporated to yield 2,2-dimethyl-4-tosyloxymethyl-1,3-dioxolane.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-ed8e1cae3379401c90de05b6d0f4ad2d
Source dataset
uspto-grants-1986_06
Patent number
US04595690

Reaction notes

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