4-Toluenesulfonyl chloride → HCID 20481468, compound

HRID 1648964Notes

Reaction equation

HRID 1648964 reaction equation
[OH:1][CH:2]1[CH2:5][O:4][CH2:3]1.[C:6]1([CH3:16])[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1.[OH-].[Na+]>O>[S:12]([C:9]1[CH:10]=[CH:11][C:6]([CH3:16])=[CH:7][CH:8]=1)([O:1][C:2]1[CH2:3][O:4][CH:5]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

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

Product 1

HCID 20481468HCID 20481468, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred suspension of 315 g of 3-hydroxyoxetane (3.4 Moles) 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 temperatures 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. temperatureice bath cooling
  2. customthe reaction temperature below 70° C
  3. customWhen the exothermic reaction
  4. custom(10 minutes)
  5. customthe cooling bath was removed
  6. customthe reaction temperatures
  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-57f12489114d4442a64418cd9bec4b42
Source dataset
uspto-grants-1983_11
Patent number
US04414384

Reaction notes

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