M-Xylene → 2,5,7-Trimethyl-1-indanone

HRID 1492735Notes

Reaction equation

HRID 1492735 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([CH3:12])[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1.Br[C:14]([CH3:19])([CH3:18])[C:15](Br)=[O:16]>C(Cl)Cl>[CH3:18][CH:14]1[CH2:19][C:9]2[C:10](=[C:5]([CH3:12])[CH:6]=[C:7]([CH3:11])[CH:8]=2)[C:15]1=[O:16]

Participants

5

Reactant 3

HCID 7929M-XyleneHCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 117690492,5,7-Trimethyl-1-indanoneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

107 g (810 mmol) of AlCl3 were slowly added to a solution of 34.4 g (324 mmol) of m-xylene (99% pure) and 74 g (324 mmol) of 2-bromoisobutyryl bromide (98% pure) in 600 ml of analytical grade methylene chloride via a solids metering funnel at room temperature, while stirring vigorously, whereupon vigorous evolution of gases started. The mixture was stirred at room temperature 15 hours, poured onto ice-water, which was acidified with 25 ml of concentrated HC1, and extracted several times with ether. The combined organic phases were washed first with a saturated NaHCO3 solution and then with a saturated NaC1 solution, and dried with magnesium sulfate. The oil which remained after the solvent had been stripped off under reduced pressure was distilled over a short distillation bridge. 52.4 g of the indanone 1 passed over at 81°-90° C./0.1-0.2 mbar in the form of a colorless oil, which crystallized at room temperature. The yield was 93%.

Workup

  1. customat room temperature
  2. stirringThe mixture was stirred at room temperature 15 hours
  3. additionpoured onto ice-water, which
  4. extractionextracted several times with ether
  5. washThe combined organic phases were washed first with a saturated NaHCO3 solution
  6. dry with materialwith a saturated NaC1 solution, and dried with magnesium sulfate
  7. distillationwas distilled over a short distillation bridge
  8. custompassed over at 81°-90° C./0.1-0.2 mbar in the form of a colorless oil, which
  9. customcrystallized at room temperature

Sources & evidence

ORD record
ord-e82e8049a3074da69f9274b9e4fc119d
Source dataset
uspto-grants-1994_12
Patent number
US05374752

Reaction notes

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