Benzene → 2-Methylindanone

HRID 357665

Reaction equation

HRID 357665 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Br[C:12]([CH3:17])([CH3:16])[C:13](Br)=[O:14]>C(Cl)Cl>[CH3:16][CH:12]1[CH2:17][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:13]1=[O:14]

Participants

5

Reactant 3

HCID 241BenzeneHCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2492622-Methylindanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.3 g (125 mmol) of AlCl3 were added to a solution of 3.91 g (50 mmol) of benzene in 30 ml of analytical grade methylene chloride, while cooling with ice. 11.9 g (52 mmol) of 2-bromoisobutyryl bromide were then added, and stirring was continued at 0° C. for 1 hour and at room temperature for 2 hours. The mixture was heated under reflux for a further 15 hours and then worked up analogously to Example A. The crude product was chromatographed on 100 g of silica gel (hexane/methylene chloride 1:1). The yield was 5.1 g (70%).

Workup

  1. temperaturewhile cooling with ice
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for a further 15 hours
  4. customThe crude product was chromatographed on 100 g of silica gel (hexane/methylene chloride 1:1)

Sources & evidence

ORD record
ord-f425ba351e92487292b7828877e57bd6
Source dataset
uspto-grants-1998_11
Patent number
US05840948

Linked notes

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