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

HRID 522639Notes

Reaction equation

HRID 522639 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.C(N(CC)CC)C.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:24][C:23]1[CH:25]=[CH:26][C:20]([S:17]([O:8][CH2:7][CH:5]2[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]2)(=[O:19])=[O:18])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 7528SolketalHCID 8471Triethylamine

Product 1

HCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonateYield 53.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (5.28 g, 40.0 mmol), triethyl amine (12.12 g, 120.0 mmol) and 4-dimethylaminopyridine (500 mg, 4.0 mmol) in dichloromethane (200 mL) was added tosyl chloride (15.2 g, 80.0 mmol). The reaction mixture was stirred at RT overnight, then quenched with water (200 mL) and extracted with ethyl acetate. The organic layers were separated, combined, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography, eluting with ethyl acetate/petroleum ether=1/8, to afford (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (6.1 g, yield 53%), MS (ES+) C13H18O5S requires: 286, found: 287 [M+H]+.

Workup

  1. customquenched with water (200 mL)
  2. extractionextracted with ethyl acetate
  3. customThe organic layers were separated
  4. washwashed with water (200 mL) and brine (200 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with ethyl acetate/petroleum ether=1/8

Sources & evidence

ORD record
ord-c0533b4f1be04c9ba55b26396eff7743
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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