Aluminum(III) Chloride → 6-tert-butyl-2,3-dihydro-1H-inden-1-one

HRID 1017147Notes

Reaction equation

HRID 1017147 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

HCID 6451240Aluminum(III) ChlorideHCID 184028883-(4-t-Butylphenyl)propionyl chloride

Product 1

HCID 184028836-tert-butyl-2,3-dihydro-1H-inden-1-oneYield 131%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. additionA 3 neck round bottom flask fit with a thermometer, nitrogen inlet, condenser, overhead stirrer, and solids addition funnel
  2. temperatureThe reaction mixture was cooled to 10 C
  3. customthe reaction
  4. customwas quenched into 5% HCl/ice (1 L)
  5. washThe organics were washed with water (10×200 mL)
  6. filtrationfiltered through celite
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvents were removed by rotary evaporation

Sources & evidence

ORD record
ord-e759c181955a4a158d0eb216a9205e4f
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

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