반응 #214733

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2-diazo-5,5-dimethylcyclohexane-1,3-dione

chlorobenzene

benzophenone

5-t-butyl-m-xylene

→

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

수율 11.0%

반응 조건

후처리

1. 1
   기타fitted with a borosilicate glass
2. 2
   여과filter
3. 3
   기타after degassing for 1 hour under nitrogen
4. 4
   추출The photolysis mixture was extracted with 0.25 N NaOH
5. 5
   세척washed with ether
6. 6
   추출extracted with chloroform
7. 7
   건조The chloroform was dried over anhydrous MgSO4
8. 8
   기타to give a crude yellow solid
9. 9
   기타the combined crude product from these ractions was chromatographed through silica gel (0.063-0.2 mm)
10. 10
    기타The solid obtained from the chromatography
11. 11
    기타was recrystallized from benzene

실험 절차

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.

출처