Thionyl Chloride → 1-Pentanesulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

1-Pentanesulfonic acid, sodium salt (10 g, 57.5 mmol) was charged into a 250 ml round bottom flask (allow headroom). Thionyl chloride (20 mL) is added; gas evolves, and a while solid forms. The mixture is heated at 60° C. for 3 hours. The solvents are removed in vacuo; toluene is added and removed in vacuo to remove residue of SOCl2. The residue is partitioned between CH2Cl2 and ice water; the organic layer is dried over Na2SO4. The crude product is purified by distillation (bp 54-56° C. @ 0.5 mm Hg) to give a clear oil, 61% yield.

Provenance & Evidence