4-Toluenesulfonyl chloride → HCID 20481468, compound

HRID 1075315Notes

Reaction equation

HRID 1075315 reaction equation
[OH:1][CH:2]1[CH2:5][O:4][CH2:3]1.[S:6]([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)([O-])(=[O:8])=[O:7].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[Na+]>O>[S:6]([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)([O:1][C:2]1[CH2:3][O:4][CH:5]=1)(=[O:8])=[O:7]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 85570p-ToluenesulfonateHCID 9942117Oxetan-3-ol

Product 1

HCID 20481468HCID 20481468, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The unpurified 3-hydroxyoxetane produced in Example 11 was used directly in the synthesis of its tosylate. To a stirred suspension of 315 g of the material (containing 3.4 moles of 3hydroxyoxetane) and 743 g (3.9 moles) of technical grade p-toluenesulfonyl chloride in 600 mL of water, was added dropwise, over a period of 25 minutes, a solution of 218 g (5.45 moles) of sodium hydroxide in 225 mL of water. The reaction was exothermic and ice bath cooling was used to keep the reaction temperature below 70° C. When the exothermic reaction subsided (10 minutes), the cooling bath was removed and the reaction temperature was allowed to decrease to 40° C. over a 1 hour period. The product was isolated by filtration, washed with four 200 ml portions of warm (45°-55° C.) water, and air dried to give 730 g (94% yield) of 3-oxetyl tosylate, mp 86°-88° C.

Workup

  1. additionwas added dropwise, over a period of 25 minutes
  2. temperatureice bath cooling
  3. customthe reaction temperature below 70° C
  4. customWhen the exothermic reaction
  5. custom(10 minutes)
  6. customthe cooling bath was removed
  7. customThe product was isolated by filtration
  8. washwashed with four 200 ml portions
  9. temperatureof warm (45°-55° C.) water, and air
  10. customdried

Sources & evidence

ORD record
ord-089eab2bd20544fc8282e7ed22f12bf5
Source dataset
uspto-grants-1983_07
Patent number
US04395561

Reaction notes

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