Chemical Properties
white to light yellow crystal powde
Uses
L(-)-10-Camphorsulfonyl chloride is a useful synthetic intermediate,it is used for asymmetric hydroxylation.
Uses
A chiral derivative of Camphor.
Synthesis
In the dry 250 mL round bottom flask with magnetic stirrer, reflux condenser tube and drying tube, add sulfoxide, cooled to 0 with an ice water bath, under stirring in batches to add camphorsulfonic acid synthesized by the above method, reacted at 0 for 1h, withdraw the ice bath, so that the natural warming, and then reacted at room temperature for another 2h, microthermal to the solution until clarified, the tail gas is absorbed by a 10% solution of sodium hydroxide. At the end of the reaction, the excess sulfoxide chloride was evaporated under reduced pressure, and the reactants were poured into crushed ice with rapid stirring, quickly filtered, washed with ice water and dried under vacuum to obtain a white powdery solid. After petroleum ether recrystallization to get the product levocamphor-10-sulfonyl chloride.
Purification Methods
If free from OH bands in the IR, then recrystallise it from Et2O or pet ether; otherwise treat it with SOCl2 at 50o for 30minutes, evaporate, dry the residue over KOH in a vacuum and recrystallise it. The (±)-acid chloride has m 85o [Bartlett & Knox Org Synth 45 14 1965]. Itis characterised as the amide (prisms from EtOH) m 132o, [ ] 17 (+) and (-) 1.5o (EtOH). On repeated recrystallisation from EtOH the anilide has m 120.5-121o, [] 25 +76o (c 1, CHCl3). [Read & Storey J Chem Soc 2761 1930, Sutherland & Shriner J Am Chem Soc 58 62 1936, Halterman et al. J Am Chem Soc 109 8105 1987, Bartlet & Knox Org Synth 45 55 1945, Beilstein 11 IV 650.]
