4-Toluenesulfonyl chloride → HCID 20481468, compound

Participants

Reaction Steps

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.

Provenance & Evidence