What are methods by which esterification using acids may be driven to higher yields?

Question

in connection with synthesis of liquid crystalline cholesteryl benzoate

Answer 1

If you cannot go the route of the acyl chloride and must use the acid you can use a Deans-Stark trap. The released water is trapped in the reflux and removed from the reaction mixture driving the reaction to higher yields (see ref).

ref: http://genchem.chem.wisc.edu/demonstrations/Gen_Chem_Pages/13equilpage/esterification_using_a_dea.htm

Answer 2

Convert the acid (benzoic acid) into an acid chloride (benzoyl chloride) before reacting it with the cholesterol. Yields approach 100% this way.