Water → 2-(4'-Methylphenyl)-5,5-dimethyl-1,3-cyclohexanedione

HRID 370385Notes

Reaction equation

HRID 370385 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](C#N)[C:9](=[O:20])[CH2:10][C:11]([CH3:19])([CH3:18])[CH2:12][C:13]([O:15]CC)=O)=[CH:4][CH:3]=1.O.S(=O)(=O)(O)O.C(OC(C)C)(C)C>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:9](=[O:20])[CH2:10][C:11]([CH3:18])([CH3:19])[CH2:12][C:13]2=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 7914Diisopropyl EtherHCID 13531594Ethyl 6-(4'methylphenyl)-6-cyano-5-keto-3,3-dimethylhexanoate

Product 1

HCID 132597702-(4'-Methylphenyl)-5,5-dimethyl-1,3-cyclohexanedioneYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 3 liter flask was equipped with a mechanical stirrer, reflux condenser, addition funnel, N2 inlet, and thermometer. The flask was charged with 156.77 g (0.52 mol) of ethyl 6-(4'-methylphenyl)-6-cyano-5-keto-3,3-dimethylhexanoate dissolved in 370 ml of glacial acetic acid, followed by 132 ml of water, and finally 132 ml of conventrated sulfuric acid was added. The reaction mixture was refluxed for 48 hours, cooled to room temperature and 600 ml of water and 300 ml of isopropyl ether added. This two-phase system was refluxed for 1 hour, cooled in an ice bath, and filtered. The precipitate was washed thoroughly with water and isopropyl ether, then dried overnight in a vacuum oven to give 68.09 g (57% yield) of the desired product as a pale yellow powder; m.p. 199.5°-201.5° C.

Workup

  1. customA 3 liter flask was equipped with a mechanical stirrer
  2. temperaturereflux
  3. additioncondenser, addition funnel, N2 inlet
  4. additionwas added
  5. temperatureThe reaction mixture was refluxed for 48 hours
  6. temperatureThis two-phase system was refluxed for 1 hour
  7. temperaturecooled in an ice bath
  8. filtrationfiltered
  9. washThe precipitate was washed thoroughly with water and isopropyl ether
  10. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-88c7bb7cb8b54b1f94ef293700ca161f
Source dataset
uspto-grants-1985_07
Patent number
US04526723

Reaction notes

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