Reaction #8381

ord-9c4c3610f2df4ee7bbd50d06f17076ad

Reaction equation

[Na+].[OH-]
sodium hydroxide
CC1(CO)COC1
3-methyl-3-oxetanemethanol
Cc1ccc(S(=O)(=O)Cl)cc1
p-toluenesulfonyl chloride
O
water
→
Cc1ccc(S(=O)(=O)CC2(C)COC2)cc1
3-METHYL-3-TOSYLMETHYLOXETANE

Reactants

—
solution
[Na+].[OH-]
sodium hydroxide
CC1(CO)COC1
3-methyl-3-oxetanemethanol
Cc1ccc(S(=O)(=O)Cl)cc1
p-toluenesulfonyl chloride
O
water

Reagents

None

Solvents

ClCCl
methylene chloride
ClCCl
methylene chloride

Conditions

Temperature
0°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added over 1 hour
  2. 2
    OtherA white precipitate formed immediately
  3. 3
    OtherThe dichloromethane solution layer was then removed
  4. 4
    Dryingdried with sodium sulfate
  5. 5
    Otherthe solvent was removed

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%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07087710B2uspto-grants-2006_08