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

HRID 65278
Notes
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Reaction equation

HRID 65278 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 23931
Mercury
Catalyst

Procedure

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 0.25N NaOH, washed with ether, acidified with 1N 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 reactions 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 244°-49° C.

Workup

  1. customfitted with a borosilicate glass
  2. filtrationfilter
  3. customafter degassing for 1 hour under nitrogen
  4. extractionThe photolysis mixture was extracted with 0.25N 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 reactions was chromatographed through silica gel (0.063-0.2 mm)
  10. customThe solid obtained from the chromatography
  11. customwas recrystallized from benzene

Sources & evidence

ORD record
ord-70011b4f8d694016b0837d15af9bff3c
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04613617

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes