Benzophenone → 2-(2',6'-Dimethyl-4'-t-butylphenyl)-5,5-dimethyl-1,3-cyclohexanedione

HRID 127551

Reaktionsgleichung

Reaktionsgleichung von HRID 127551
[N+](=[C:3]1[C:8](=[O:9])[CH2:7][C:6]([CH3:11])([CH3:10])[CH2:5][C:4]1=[O:12])=[N-].ClC1C=CC=CC=1.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:34]([C:38]1[CH:39]=[C:40]([CH3:45])[CH:41]=[C:42]([CH3:44])[CH:43]=1)([CH3:37])([CH3:36])[CH3:35]>[Hg]>[CH3:45][C:40]1[CH:39]=[C:38]([C:34]([CH3:36])([CH3:35])[CH3:37])[CH:43]=[C:42]([CH3:44])[C:41]=1[CH:3]1[C:8](=[O:9])[CH2:7][C:6]([CH3:11])([CH3:10])[CH2:5][C:4]1=[O:12]

Komponenten

6

Edukt 4

HCID 3102BenzophenoneHCID 73785-Tert-butyl-m-xyleneHCID 7964ChlorobenzeneHCID 353445Diazodimedone

Produkt 1

HCID 125563382-(2',6'-Dimethyl-4'-t-butylphenyl)-5,5-dimethyl-1,3-cyclohexanedioneAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23931MercuryKatalysator

Versuchsvorschrift

A solution of 7.00 g (0.042 mol) of 2-diazo-5,5-dimethylcyclohexane-1,3-dione in 300 ml of 5-t-butyl-m-xylene and 250 ml chlorobenzene containing 38.38 g (0.21 mol) of benzophenone was irradiated overnight with a 200 watt mercury arc lamp fitted with a borosilicate glass filter after degassing for 1 hour under nitrogen. The photolysis mixture was extracted with 0.25 N NaOH, washed with ether, acidified with 1 N HCl, and extracted with chloroform. The chloroform was dried over anhydrous MgSO4 and stripped to give a crude yellow solid. The photolysis was repeated and the combined crude product from these ractions was chromatographed through silica gel (0.063-0.2 mm) using benzene-ethyl acetate. The solid obtained from the chromatography was recrystallized from benzene to give 2.76 g (11%) of 2-(2',6'-dimethyl-4'-t-butylphenyl)-5,5-dimethyl-1,3-cyclohexanedione as white crystals, mp 224°-49° C.

Aufarbeitung

  1. customfitted with a borosilicate glass
  2. filtrationfilter
  3. customafter degassing for 1 hour under nitrogen
  4. extractionThe photolysis mixture was extracted with 0.25 N NaOH
  5. washwashed with ether
  6. extractionextracted with chloroform
  7. dry with materialThe chloroform was dried over anhydrous MgSO4
  8. customto give a crude yellow solid
  9. customthe combined crude product from these ractions was chromatographed through silica gel (0.063-0.2 mm)
  10. customThe solid obtained from the chromatography
  11. customwas recrystallized from benzene

Quellen und Nachweise

ORD-Eintrag
ord-f865d0a0bb5045e6be6e3838ea1d8289
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256657

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