Hydrochloric Acid → 5-(Isopropyl)cyclohexane-1,3-dione

HRID 649358Notes

Reaction equation

HRID 649358 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Na].C(OCC)(=O)CC(OCC)=O.[CH3:17][CH:18]([CH3:24])[CH:19]=[CH:20][C:21](=[O:23])[CH3:22].[OH-].[K+].Cl>O.C(O)C>[CH:18]([CH:19]1[CH2:20][C:21](=[O:23])[CH2:22][C:2](=[O:1])[CH2:3]1)([CH3:24])[CH3:17]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 14797Potassium HydroxideHCID 212445-Methylhex-3-en-2-oneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 5661065-(Isopropyl)cyclohexane-1,3-dioneYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a fresh solution of sodium ethoxide prepared from 23 g (1.0 mole) of sodium and 700 ml of absolute ethanol is added 168.2 g (1.05 mole) of diethyl malonate and 114.24 g (1.02 mole) of distilled 5-methyl-3-hexene-2-one. The mixture is refluxed for 1 hour; an additional 125 ml of ethanol added; and refluxing continued for two more hours. A solution of 123.4 g of potassium hydroxide in a 600 ml of water is then added and the reaction mixture refluxed for 6 hours. The mixture is then neutralized with 12% hydrochloric acid to pH 4. The ethanol is distilled and the mixture treated with three 15 g portions of activated charcoal. The hot reaction mixture is filtered through filter aid after acidification to pH 2. The product is extracted with hot isopropyl ether (700 ml). Cooling of the isopropyl ether layer results in 60.5 g (40% yield) of the product, m.p. 52°- 65° C.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. temperatureand refluxing
  3. temperaturethe reaction mixture refluxed for 6 hours
  4. distillationThe ethanol is distilled
  5. additionthe mixture treated with three 15 g portions of activated charcoal
  6. filtrationThe hot reaction mixture is filtered
  7. filtrationthrough filter aid after acidification to pH 2
  8. extractionThe product is extracted with hot isopropyl ether (700 ml)
  9. temperatureCooling of the isopropyl ether layer

Sources & evidence

ORD record
ord-968b2b9140714b9bb96a4f6162e7c6d5
Source dataset
uspto-grants-1988_04
Patent number
US04739114

Reaction notes

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