Acetic Acid → 2-(2,4-Dimethylphenyl)-5,5-dimethylcyclohexane-1,3-dione

HRID 127536

Reaktionsgleichung

Reaktionsgleichung von HRID 127536
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH:9](C#N)[CH2:10][CH2:11][C:12]([CH3:20])([CH3:19])[CH2:13][C:14]([O:16]CC)=O.Cl.C(O)(=[O:26])C.O>C(OCC)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:10](=[O:26])[CH2:11][C:12]([CH3:19])([CH3:20])[CH2:13][C:14]1=[O:16]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 962Water2×HCID 13688117Ethyl 6-(2',4'-dimethylphenyl)-6-cyano-3,3-dimethylhexanoate

Produkt 1

HCID 125563452-(2,4-Dimethylphenyl)-5,5-dimethylcyclohexane-1,3-dioneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A one-neck round bottom flask was charged with 52.50 g (0.17 mol) of ethyl 6-(2',4'-dimethylphenyl)-6-cyano-3,3-dimethylhexanoate, 250 ml of concentrated hydrochloric acid, 250 ml of glacial acetic acid, and 100 ml of water. The reaction mixture was stirred and refluxed for 48 hours. After 12 hours and 24 hrs. of refluxing, an additional 100 ml of conc. HCl and 100 ml glacial HOAC were added. After 48 hours, the mixture was stripped to dryness under reduced pressure. To the residue were added 150 ml of water and 150 ml of ethyl ether, and the mixture shaken vigorously. A white, crystalline precipitate formed, and this was removed by suction filtration to give 13.20 g (32%) of 2-(2',4'-Dimethylphenyl)-5,5-dimethyl-1,3-cyclohexanedione as a white, crystalline solid, m.p. 167°-168.5° C.

Aufarbeitung

  1. temperaturerefluxed for 48 hours
  2. custom24 hrs
  3. temperatureof refluxing
  4. waitAfter 48 hours
  5. stirringthe mixture shaken vigorously
  6. customA white, crystalline precipitate formed
  7. customthis was removed by suction filtration

Quellen und Nachweise

ORD-Eintrag
ord-296349d9757f465ab58d85f80acef677
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256658

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