[tdzeta]

Problem: I tried TosOH/DCM protocol for THP-protection of my alcohol, but I always have a lot of impurities derived from DHP self-reaction. It is impossible to clean my THP-prptected alcohol from these by products by cc-sg

Question: Could you share a good protocol which can yield a clean THP-protected alcohol without the impurities?

Thank you in advance! 

[AlphaScent]

What is your compound structure?

What other functional groups are present?

[tdzeta]

It is not important. It has only one naked -OH and by-products are from DHP self condensation. I am going to reduce temp. down to 0°C or so on. I feel this should help as  DHP reacts with -OH much faster than with DHP.

[orgopete]

I don't know the answer to your question, but as an experimentalist, if I was observing self condensation of my reagent, I'd reduce the stoichiometry or I'd add it slowly.

[PhDoc]

Why are you using THP group?

Benzyl, BOM, MEM, MOM, TBS, TBDPS, SEM... see Theodora Greene

[tdzeta]

I use THP because it is hard to de-protect this -OH (if other protective group is used) and the protection is required as the reaction condition is way too hard for this molecule to survive.

The Green's book is a great one but I did not find  any information about DHP by-products I see in my reaction mixture in there. It should be ascribed-discussed somewhere I believe, but I still could not find such paper etc.