[H2lickwid]

I am trying to propose a plausible mechanisms for the reaction at the top of the page. I initially thought that a substitution is the only way to make the seven membered ring but realized that a sunstitution on the benzene is very unlikely. Is there a way that a Michael addition is a plausible way for this mechanisms to proceed? What are your ideas?

[orgopete]

Hint, first step conjugate addition?

[phth]

The red arrows: what aromatic substitution mechanism do you think it undergoes?  Hint: its not SN2

[orgopete]

The red arrows: what aromatic substitution mechanism do you think it undergoes?  Hint: its not SN2

Are you proposing the Ar-O bond becomes broken? I don't think it does.

[phth]

Pete: I mean E1cB

[H2lickwid]

Thank you for your replies. I initially thought this proceeded via an sn2 mechanism but realize that it is very unlikely. The ec1b seems much more likely, thank you!!!

[orgopete]

I don't agree with the curved arrow mechanism. I think it is a conjugate addition, deprotonation of the hemiacetal to form the aldehyde and phenoxide, and then an alkylation of the phenoxide with the bromide.