Sodium Hydroxide → N-(3-Benzyloxypropoxymethyl)-2,4,6-trichloro-N-methylbenzenesulfonamide

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Reaction Steps

A soln. of 3-benzyloxy-1-propanol (4.08 g, 3.90 ml, 24.5 mmol) and tetra-n-butylammonium hydrogen sulfate (1.78 g, 5.25 mmol) in toluene (100 ml) was cooled in an ice-bath and 35% strength sodium hydroxide solution (49.0 g, 140 ml, 1.22 mol) was added. A soln. of 2,4,6-trichloro-N-chloromethyl-N-methylbenzenesulfonamide (7.10 g, 22 mmol) in MC (60 ml) was then slowly added dropwise. The mixture was then stirred at RT for 15-20 h. Thereafter, the phases were separated and the organic phase was washed neutral with water (6×50 ml) and saturated sodium chloride solution (2×40 ml), dried with Na2SO4 and concentrated i. vac. The crude product was purified by means of flash chromatography with cyclohexane/EtOAc (9:1).

Provenance & Evidence