1,3,5-Triiodo-2,4,6-trimethylbenzene → 3,5-Dioxohexanoic acid

Reaction equation

IC1C(C)=C(I)C(C)=C(I)[C:3]=1[CH3:12].[Mn]([O-])(=O)(=O)=O.[K+].C([O:22][C:23](=[O:25])[CH3:24])(=O)C.[C:26]([OH:29])(=O)[CH3:27].S(=O)(=O)(O)[OH:31]>>[CH3:12][C:3]([CH2:27][C:26]([CH2:24][C:23]([OH:22])=[O:25])=[O:29])=[O:31]

Participants

Reactant 2

HCID 6356131,3,5-Triiodo-2,4,6-trimethylbenzene

HCID 131725874Potassium permanganate acetic anhydride acetic acid sulfuric acid

Product 1

HCID 54598443,5-Dioxohexanoic acidYield 35%

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%.

Sources & evidence

ORD record: ord-4dd019e84355481ab7d6cab2142e4e33
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07083516B2

Reaction notes

Loading…