Water → 3-Methyl-3-[(4-methylbenzene-1-sulfonyl)methyl]oxetane

HRID 8285Notes

Reaction equation

HRID 8285 reaction equation
[CH3:1][C:2]1([CH2:6]O)[CH2:5][O:4][CH2:3]1.[OH-].[Na+].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.O>C(Cl)Cl>[CH3:1][C:2]1([CH2:6][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH2:5][O:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 1378373-Methyl-3-oxetanemethanol

Product 1

HCID 220152623-Methyl-3-[(4-methylbenzene-1-sulfonyl)methyl]oxetane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-methyl-3-oxetanemethanol (100 g, 0.98 mol) was dissolved in 250 mL methylene chloride, and a 35% solution of sodium hydroxide (143.60 g, 1.08 mol)was added, and the reaction was cooled to 0° C. A solution of p-toluenesulfonyl chloride was added (186.67 g, 0.98 mol) in 375 mL methylene chloride was added over 1 hour. A white precipitate formed immediately. The reaction was stirred for 10 additional hours. 1000 mL of water was added. The dichloromethane solution layer was then removed, and dried with sodium sulfate, and the solvent was removed. Yield: 217.77 grams of 3-methyl-3-tosylmethyloxetane as white crystals, 87%.

Workup

  1. additionwas added over 1 hour
  2. customA white precipitate formed immediately
  3. customThe dichloromethane solution layer was then removed
  4. dry with materialdried with sodium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-9c4c3610f2df4ee7bbd50d06f17076ad
Source dataset
uspto-grants-2006_08
Patent number
US07087710B2

Reaction notes

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