Hi, im running into some troubles with esterification of methol.
Im doing this reaction (pic): Im doing it in refluxing toluene with 1eq of catalyst (pyridine, DMAP etc) but no matter what I do I always get only about 50% conversion even when I use excess of menthol. I tried DCC+DMAP in DCM with the parent acid and got similar resuts. I tried to make metholate with NaH but didnt realy work either. I can collumn the product easily but since it is 2nd step and i need to do some 4 more AND Im gonna need more than few mg of the final product Im looking to improve the yield (usualy about 45-55% after CC).
Any ideas what might cause the lack of reactivity? Since the starting materials are fairly cheap Im kinda OK with doing it large scale and get only 50% but obviously, better yield is always better this early in synthesis