DMAP as a Phase Transfer Catalyst

DMAP acts as an inverse phase transfer catalyst (IPTC) for the reaction of water-insoluble acid chlorides with aqueous D,L-Alanine. Alanine was converted to the amide in 85 percent yield (after 10 minutes) on trea®ent with p-chlorobenzoyl chloride and DMAP. No conversion was observed in the absence of DMAP after 10 Minutes¹.

Another example of DMAP's IPTC capability is provided below²:

1. L. J. Mathias and R. V. Vaida, J. Am. Chem. Soc., 108, 1093 (1986).
2. K. C. Waterman and A. Streitweiser, Jr., J. Am. Chem. Soc., 106, 3874 (1984).