Aluminum(III) Chloride → 6-tert-butyl-2,3-dihydro-1H-inden-1-one
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13](Cl)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[C:9]2[C:8]([CH2:11][CH2:12][C:13]2=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 3 neck round bottom flask fit with a thermometer, nitrogen inlet, condenser, overhead stirrer, and solids addition funnel was charged with 3-(4-t-butylphenyl)propionyl chloride (99.0 g, 0.442 mol) and methylene chloride (2.0 L). The reaction mixture was cooled to 10 C. and aluminum chloride (62.1 g, 0.466 mol) was added slowly to the reaction mixture. After allowing the reaction to warm to room temperature and stir overnight the reaction was quenched into 5% HCl/ice (1 L). The organics were washed with water (10×200 mL), filtered through celite, and dried over anhydrous sodium sulfate. The solvents were removed by rotary evaporation to yield the crude 6-t-butyl-1-indanone (109 g). 1HNMR (CDCl3, 500 MHz) δ7.79 (d, J=1.5 Hz, 1H); 7.66 (dd, JAB=2.8 Hz, 1H); 7.42 (d, J=8 Hz, 1H); 3.10 (t, J=6 Hz, 2H); 2.70 (t, J=6 Hz, 2H); 1.34 (s, 9H).