[Sarvan_RTK]

Mechanism and Retrosynthesis

I have a doubt from the book: Organic synthesis the disconnection approach (Stuart warren 2nd edition) on page 49. How primary alcohol (compound 60) reacts with an aldehyde and HCl to give the intermediate 61 and then cyclise to form 58. Please advise mechanism.

[rolnor]

Can you post a picture? I dont think everyone has that book.

[Sarvan_RTK]

Many Thanks. I posted the picture. Please advise me of the mechanism. How aldehyde and alcohol, and HCl give intermediate and form the final product. I could understand the last step. But I could not understand the first step. Please help.

[rolnor]

The first step is similar to acetal formation but the chloride ion attacks instead of the alcohol in the second step:
https://en.wikipedia.org/wiki/Acetal

[Babcock_Hall]

@OP, What are your thoughts?

[Sarvan_RTK]

Thanks. Is there any chance to see the arrow pushing mechanism here? Is there any chance to see the arrow pushing mechanism here? 

[Babcock_Hall]

Sarvan_RTK,

Please look at the forum rules (see red link above), and show us your work.  We can only help you after that.

[Sarvan_RTK]

This looks like phenyl isochromane synthesis

Synthesis of isochromans via Fe(OTf)2-catalyzed Oxa-Pictet–Spengler cyclization

[rolnor]

No, its rather a case of Friedel-Craft alkylation. I think you need a Lewis acid for the last step.