[Walnuts]

Eugenol is a phenol is unpolor and after distillation loses its -OH and its replaced with -OCOCH2 (I think) for acyteleugenol also unpolar. Solvent is Dichloromethane which has no -NH2 or -OH group so solubility its just based off polarity? No reaction because no -NH2 or -OH correct?

[wildfyr]

Just based on gut alone, I bet both eugenol and acetyleugenol are soluble in DCM. I am also not entirely sure this answers your question. I also dont see how distillation causes acetylation.