I've been trying to remove a benzyl protecting group of a phenol and also remove a CBZ protecting group on a secondary amine by standard hydrogenation of the material with 10% Pd on Carbon. My protected molecule is very lipophilic and soluble in DCM. The reason I added methanol was because the intermediates generated (the intermediate where the benzyl is removed but the CBZ still present and vice versa) are generally not soluble in DCM, but soluble in methanol. Deprotection of the two groups worked fine, but to my surprise, after working up the reaction, my material is a salt. I definitely know it is a salt because of the broadening of the NMR signals. I'm just not sure where the acid is coming from or even what acid it is. I know a good way to dehalogenate material is by hydrogenation with Pd on carbon. Am I dehalogenating the DCM ,and with the presence of methanol as well, generating HCl which is reacting with the amine moities to generate a HCl salt?