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

HRID 1789037Notes

Reaction equation

HRID 1789037 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>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([O:8][CH2:7][CH:5]2[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]2)(=[O:18])=[O:17])=[CH:12][CH:11]=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

To a solution of 7.2 g of 2,2-dimethyl-1,3-dioxolan-4-ylmethanol in 40 ml of pyridine at 0° C. was added 11.3 g of p-toluenesulfonyl chloride in portions. The solution was kept at 25° C. for 48 hours, then poured into water and extracted with diethyl ether. The organic solution was washed twice with water, once with dilute hydrochloric acid and once with dilute sodium carbonate solution. The organic solution was dried with magnesium sulfate and evaporated under vacuum to yield (±)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic solution was washed twice with water, once with dilute hydrochloric acid and once with dilute sodium carbonate solution
  3. dry with materialThe organic solution was dried with magnesium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-5b2332c698da4b758551572ce287cd08
Source dataset
uspto-grants-1987_08
Patent number
US04686234

Reaction notes

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