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

HRID 1913854Notes

Reaction equation

HRID 1913854 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.C(Cl)Cl.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>O>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][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

5

Reactant 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 7528Solketal

Product 1

HCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonateYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.3 g, 1.2 ml (10 mmol) of Dimethyl-1,3-dioxolane-4-methanol, 3.7 g (3.0 mmol, 3.0 eq) of 4-Dimethyl amino pyridine dried for one hour was added and dissolved with 100 mL of CH2Cl2. Thereafter, 2.3 g (12 mmol, 1.2 eq) of p-Toluenesulfonyl chloride was added, then, [the solution] was stirred for the first 30 minutes dipped in cold water at room temperature under argon atmosphere (colorless transparent). After stirring for 18 hours, the disappearance of the raw materials was checked by TLC, liquid separation was carried out with a separating funnel (organic solvent: CDCl3) and the oil layer was dried with anhydrous Na sulfate. An hour later, cotton plug-filtered and concentrated with an evaporator, [the solution] was the target compound was isolated by silica gel column chromatography (CHCl3→CHCl3:MeOH=100 to 10:1) to obtain an oily liquid (2) (pale yellow transparent to colorless transparent). The obtained liquid was dried overnight and an NMR measurement was carried out. (yield: 1.85 g, 8.3 mmol; yield 83%)

Workup

  1. additionwas added
  2. stirringAfter stirring for 18 hours
  3. customthe disappearance of the raw materials was checked by TLC, liquid separation
  4. customwas carried out with a separating funnel
  5. dry with material(organic solvent: CDCl3) and the oil layer was dried with anhydrous Na sulfate
  6. filtrationAn hour later, cotton plug-filtered
  7. concentrationconcentrated with an evaporator
  8. customwas isolated by silica gel column chromatography (CHCl3→CHCl3:MeOH=100 to 10:1)

Sources & evidence

ORD record
ord-62a5839e927348f7a65011705c6db47e
Source dataset
uspto-grants-2013_12
Patent number
US08609826B2

Reaction notes

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