Water → Glycidyl tosylate

Participants

Reaction Steps

To a solution of 10 g of 3-chloro-1,2-propanediol (0.09 mol) and 40 ml of water, was added dropwise at 24-26° C. 16.6 g of 24% sodium hydroxide (0.1 mol). The solution was stirred for one hour. The solution was cooled and thereto 0.17 g of N,N-dimethylaminopyridine (0.0014 mol) and 17.2 g of p-toluenesulfonyl chloride (0.09 mol) in 50 ml of toluene, and then 16.6 g of 24% sodium hydroxide (0.1 mol) were added under stirring at 0-5° C. And the solution was stirred for one hour. After separation with a separating funnel, the organic layer was washed with 50 ml of 1% hydrochloric acid and 50 ml of water. The excess solvent was removed under vacuo. The chemical purity by HPLC at that time was 98.3%. The residue was recrystallized from isopropyl alcohol/hexane=1/1 (V/V) to give 14.0 g of glycidyl tosylate. Chemical purity: 99.6% (yield: 68%)

Provenance & Evidence