3,3-dimethyl-5-oxohexanoic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5 parts of 5-keto-3,3-dimethylhexanoic acid and about 15 parts of 73% sulfuric acid was heated for one hour in a 130°-135° oil bath. The cooled solution was then poured into a separatory funnel containing ice and chloroform. The aqueous phase was then washed three times with additional chloroform. The combined organic extractions were then dried and evaporated. There was obtained an 82.3% yield of dimedone. It was further recrystallized from toluene. The cooled solution was then poured into a separatory funnel The aqueous phase was then washed three times with additional chloroform The combined organic extractions were then dried evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The above oxidation procedure was repeated, except that in place of periodate there was utilized sodium hypochlorite. There was added slowly about 2700 parts of an aqueous 5% sodium hypochlorite solution to a solution of 56 parts of isophorone in about 200 parts of methylene chloride. An exothermic reaction resulted causing the methylene chloride to reflux. The organic phase was analyzed shortly after the addition was complete and it was found that all of the isophorone had reacted. The aqueous layer was made basic with sodium carbonate and the reaction mixture was filtered. The aqueous phase was washed with methylene chloride and then acidified by slowly adding it to a 2 phase mixture of concentrated hydrochloric acid and methylene chloride. The organic phase was separated and the aqueous phase was extracted with several portions of fresh methylene chloride. Upon combining the various organic layers which were dried and evaporated, there was obtained 37.7 parts of 5-keto-3,3-dimethylhexanoic acid. An exothermic reaction resulted to reflux after the addition had reacted the reaction mixture was filtered The aqueous phase was washed with methylene chloride by slowly adding it to a 2 phase mixture of concentrated hydrochloric acid and methylene chloride The organic phase was separated the aqueous phase was extracted with several portions of fresh methylene chloride were dried evaporated

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isophorone (138 g) and 30% hydrogen peroxide (730 g) are dissolved in isopropanol (500 ml), and the solution is cooled to 15° C. 3N Sodium hydroxide solution (800 ml) is added slowly over a three-hour period to maintain the temperature of the reaction below 20° C. by adjusting the addition rate of sodium hydroxide solution and cooling with an ice-water bath. The reaction is allowed to warm to ambient temperature while stirring for 16 hours. The reaction mixture is extracted once with isopropyl ether (200 ml) then treated with sodium bisulfite (40 g) and acidified to pH 2 with concentrated hydrochloric acid (225 ml). The solution is extracted twice with methylene chloride (200 ml) and the resulting methylene chloride solution stripped under vacuum at 40° C., 10 mm Hg to give 3,3-dimethyl-5-ketohexanoic acid as a residue product. to maintain the temperature of the reaction below 20° C. cooling with an ice-water bath to warm to ambient temperature The reaction mixture is extracted once with isopropyl ether (200 ml) then treated with sodium bisulfite (40 g) The solution is extracted twice with methylene chloride (200 ml) stripped under vacuum at 40° C.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 16 g of isophorone in 100 g of dichloromethane was cooled down to 0° C. A stream of oxygen, which contained about 4 percent of ozone, was conducted through this solution until the solution was saturated with ozone. Then the ozonolyzed solution was added drop by drop into 150 ml of boiling water, the dichloromethane was distilled off and the aqueous solution was boiled for another 3 hours. The 3,3-dimethyl-5-oxo-hexanoic acid formed was isolated by reducing under vacuum. the dichloromethane was distilled off

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 15.8 g of isophorone in 110 ml of water was cooled down to 0° C. Then a stream of oxygen which contains about 4 percent of ozone was introduced until the suspension was saturated with ozone. The entire matter was now heated to 95° C. and was boiled for 3 hours under reflux. The 3,3-dimethyl-5-oxo-hexanoic acid was subsequently isolated by evaporation of water under vacuum. was introduced until the suspension The entire matter was now heated to 95° C. under reflux

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The process of the invention converts isophorone into an ozone-addition product, which is then converted into 3,3-dimethyl-5-oxo-hexanoic acid. From the latter, 3,3-dimethylglutaric acid is produced by means of hydrogen peroxide treatment.