Benzene → 3-Methyl-indan-1-one
Reaction equation
[C:1](O)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[Al+3].[Cl-].[Cl-].[Cl-].[CH:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:4][CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:1](=[O:5])[CH2:2]1Participants
4
Procedure
A solution of crotonic acid (20 g, 0.232 moles) in benzene (147 ml) was added AlCl3 (93 g, 0.748 moles) and the mixture was refluxed for 7 hours. Completion of the reaction was monitored by HPLC & GC. Excess benzene was distilled off and the reaction mixture was poured slowly into ice cold HCl. The organic compound was extracted with ethylacetate. The organic phase was washed thoroughly with water, dried, and evaporated under vacuum. The resultant oil was purified by high vacuum distillation (90-94° C. at ˜2 mm) giving 25 g (74%) of 99.2% pure 3-methyl-indan-1-one.
Workup
- temperaturethe mixture was refluxed for 7 hours