Water → 3,3-Dimethyl-5-oxohexanoic acid

HRID 1759445Notes

Reaction equation

HRID 1759445 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4](C)=[CH:3]1.I([O-])(=O)(=O)=[O:12].[Na+].[OH2:17]>[Ru]=O.CC(C)=O>[O:17]=[C:4]([CH3:3])[CH2:5][C:6]([CH3:8])([CH3:7])[CH2:9][C:2]([OH:1])=[O:12]

Participants

6

Reactant 3

HCID 962Water2×HCID 6544IsophoroneHCID 23667635Sodium periodate2×

Product 1

HCID 113326103,3-Dimethyl-5-oxohexanoic acidYield 63%

Reagents, catalysts & solvents 2

HCID 178527103HCID 178527103, compoundCatalystHCID 180AcetoneSolvent2×

Procedure

There was added 0.15 part of solid ruthenium oxide to a solution of 2.8 parts of isophorone and 2.5 parts of sodium periodate in about 200 parts of acetone to 40 parts of water. The resulting yellow solution was stirred while 5 parts of sodium periodate, 50 parts of water and 20 parts of acetone was added over an hour. The resulting suspension was stirred 48 hours at room temperature then filtered through Celite. The resulting filtrate was then extracted with methylene chloride. The organic phase was extracted with CHCl3. Acidification of the base washings provided 2 parts, or a 63% yield of 5-keto-3,3-dimethylhexanoic acid.

Workup

  1. additionwas added over an hour
  2. filtrationthen filtered through Celite
  3. extractionThe resulting filtrate was then extracted with methylene chloride
  4. extractionThe organic phase was extracted with CHCl3
  5. customAcidification of the base washings provided 2 parts

Sources & evidence

ORD record
ord-ad14ff663cc34751aca884fecdae2fab
Source dataset
uspto-grants-1982_07
Patent number
US04340753

Reaction notes

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