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.
About Marc Halpern
Dr. Halpern is founder and president of PTC Organics, Inc., the only company dedicated exclusively to developing low-cost high-performance green chemistry processes for the manufacture of organic chemicals using Phase Transfer Catalysis. Dr. Halpern has innovated PTC breakthroughs for pharmaceuticals, agrochemicals, petrochemicals, monomers, polymers, flavors & fragrances, dyes & pigments and solvents. Dr. Halpern has provided PTC services on-site at more than 260 industrial process R&D departments in 37 countries and has helped chemical companies save > $200 million. Dr. Halpern co-authored five books including the best-selling “Phase-Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives” and has presented the 2-day course “Practical Phase-Transfer Catalysis” at 50 locations in the US, Europe and Asia.
Dr. Halpern founded the journal “Industrial Phase-Transfer Catalysis” and “The PTC Tip of the Month” enjoyed by 2,100 qualified subscribers, now beyond 130 issues. In 2014, Dr. Halpern is celebrating his 30th year in the chemical industry, including serving as a process chemist at Dow Chemical, a supervisor of process chemistry at ICI, Director of R&D at Sybron Chemicals and founder and president of PTC Organics Inc. (15 years) and PTC Communications Inc. (20 years). Dr. Halpern also co-founded PTC Interface Inc. in 1989 and PTC Value Recovery Inc. in 1999. His academic breakthroughs include the PTC pKa Guidelines, the q-value for quat accessibility and he has achieved industrial PTC breakthroughs for a dozen strong base reactions as well as esterifications, transesterifications, epoxidations and chloromethylations plus contributed to more than 100 other industrial PTC process development projects.
Dr. Halpern has dedicated his adult life to his family and to phase-transfer catalysis (in that order!).
