Please suggest a method to do ester hydrolysis (-OAc group to tertiary -OH) in neutral media. Both acidic and basic hydrolysis is not working for my compound.
Try La(OTf)3 in methanol. Use 1 mM lanthanum triflate, 1 mM methoxide and your substrate at ~100 mM at room temperature. The reaction will give you methyl acetate and your alcohol. If you want the reaction to go faster simply use more La/methoxide but keep the ratio 1:1. Other forms of La that can be used include perchlorate salts and iodides but LaCl3 or the oxide will NOT work. See Organic and Biomolecular Chemistry 2005, 65. The second order rate constant for reaction of isopropyl acetate is about 0.004 M-1s-1. And for the record if you combine La and methoxide in a ratio of 1:1 the pH will be ~8.7 which is neutral pH in methanol.
In many cases this has worked : 1)Add catalytic amount of K2CO3 to the methanolic solution and stirr to completion. 2)Boric acid added to methanolic solution also does the job through ester exchange. Good Luck!