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

HRID 482254Notes

Reaction equation

HRID 482254 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-toluenesulfonateYield 88.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

18.8 ml (151 mmol) (2,2-dimethyl-[1,3]dioxolan-4-yl) -methanol and 28.6 g (150 mmol) toluene-4-sulfonyl chloride were stirred for 16 h at room temperature in 7 ml pyridine, it was poured onto 400 ml water, extracted twice with ethyl acetate, the combined ethyl acetate phases were washed with water, the organic phase was dried with sodium sulfate, filtered, the solvent was removed in a vacuum and 38.2 g (88%) toluene-4-sulfonic acid-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-ester was obtained as a colourless oil. MS (m/e)=286.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washthe combined ethyl acetate phases were washed with water
  3. dry with materialthe organic phase was dried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed in a vacuum

Sources & evidence

ORD record
ord-e68ebdd8183a48dca954314423607563
Source dataset
uspto-grants-1998_08
Patent number
US05795892

Reaction notes

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