Phase-transfer catalysis is known to transfer and activate acids such as HCl, HBr, HI, HNO3 and others from the aqueous phase into the organic phase through hydrogen bonding of the acid proton to the halide of a quat salt such as TBAB. So, it is a pretty good idea to apply PTC conditions to transfer HClO into a nonpolar organic solvent and react it under mild conditions.
HClO is well known to add to alkenes to form chlorohydrins. I am not familiar with the reaction that would continue to convert the chlorohydrin or otherwise cleave the alkene then wind up with the benzal group (dichloromethyl).
Earlier this year, our audience helped us identify a reaction with which I was not familiar. Can you help me again this month? Please contact Marc Halpern at PTC Organics with your answer and specify if you authorize us to publish your name and company affiliation in next month’s PTC Tip of the Month.