Reaction #6662

ord-4dd019e84355481ab7d6cab2142e4e33

Reaction equation

Cc1c(I)c(C)c(I)c(C)c1I
Triiodomesitylene
CC(=O)O.CC(=O)OC(C)=O.O=S(=O)(O)O.[K+].[O]=[Mn](=[O])(=[O])[O-]
potassium permanganate acetic anhydride acetic acid sulfuric acid
→
CC(=O)CC(=O)CC(=O)O
triacetate
Yield 35.0%

Reactants

Cc1c(I)c(C)c(I)c(C)c1I
Triiodomesitylene
CC(=O)O.CC(=O)OC(C)=O.O=S(=O)(O)O.[K+].[O]=[Mn](=[O])(=[O])[O-]
potassium permanganate acetic anhydride acetic acid sulfuric acid

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Triiodomesitylene is converted under acetylating conditions in an oxidation reaction with potassium permanganate/acetic anhydride/acetic acid/sulfuric acid into triacetate (yield: 35%). The triacetate is isolated and saponified with potassium carbonate in methanol to tris alcohol (yield: 94%). The tris alcohol is then reacted to form tris aldehyde by Swern oxidation in dimethyl sulfoxide as a solvent in a yield of 67%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07083516B2uspto-grants-2006_08