I'm on research of organic synthesis that using p-anisaldehyde as a precursor. I want to chlorinated the p-anisaldehyde in aqueous media. I've searched for journal that talking about this topic, but the most relevant is only about oxidative chlorination of some aromatic compound in aqueous media by Sharma et al. And they didn't use p-anisaldehyde as one of their reactant. However, I've tried to apply Sharma's method in journal to my reactant and it doesn't work. Therefore, is there anyone here that is mastering or has done same topic? I appreciate all answers and experiences. Thank you.
I presume, you want to prepare 3-chloro-4-methoxybenzaldehyde by the chlorination, if not, please correct. This seems to be difficult, especially in water, as the oxidation of the aldehyde group would go easier than the electrophilic attack on the ring. A similar chlorination can be done preparatively starting from isovanillin in DCM (http://journals.tubitak.gov.tr/chem/issues/kim-10-34-2/kim-34-2-3-0904-14.pdf), but I think p-anisaldehyde is not sufficiently active toward the ring substitution, so under similar conditions you will obtain mostly the corresponding benzoic acid or benzoyl chloride (probably, chlorinated).
Putra,
This reaction has been done in methanol but not in water, see
--- Hathaway, Bruce A. et al Synthetic Communications, 44(5), 660-664; 2014
***You can perform this reaction in methylene chloride using tin chloride and lead tetraacetate, see
--- Muathen, Hussni A. Tetrahedron, 52(26), 8863-8866; 1996
***You can also perform this reaction in acetonitrile using N-chlorosuccinimide, see
--- Ngi, Samuel Inack et al Advanced Synthesis & Catalysis, 355(14-15), 2936-2941; 2013
Good luck
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