2-Indanone → 2-Indanone

HRID 1289271Notes

Reaction equation

HRID 1289271 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[C:5]1([CH3:13])[CH:10]=[CH:9][C:8]([Mg]Br)=[CH:7][CH:6]=1.[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C:15]1=[O:23]>C1COCC1>[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C:15]1=[O:23].[C:5]1([CH3:13])[CH:10]=[CH:9][C:8]([C:15]2([OH:23])[CH2:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14]2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 119832-IndanoneHCID 24636Cerium(III) chlorideHCID 178418370HCID 178418370, compound

Product 2

HCID 119832-IndanoneHCID 18690301HCID 18690301, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of anhydrous cerium chloride (40.60 g, 164.7 mmol) in THF(250 mL) was stirred at room temperature for 2 hours under nitrogen. p-Tolylmagnesium bromide (100.0 mL of 1.0M solution in diethyl ether, 100.0 mmol) was added at 0° C. and stirred for 3.5 h. A solution of 2-indanone (14.21 g, 107.7 mmol) in THF (20 mL) was added at the same temperature. After stirring at 0° C. for 3 h, the mixture was allowed to warm to room temperature and kept at ambient temperature overnight (12 h). It was then treated with 5% aqueous hydrochloric solution. The solution was extracted with diethyl ether (4*200 mL). All etheral layers were combined, washed with water (100 mL), dried over anhydrous magnesium sulphate and concentrated to give the crude product. Kugelrohr distillation yielded 2.94 g of 2-indanone (110° C./0.3 mm Hg) and 17.27 g of 2-(p-tolyl)-2-indanol (160° C./0.3 mm Hg) in solid form. 1H-N.M.R. (CDCl3) d 2.17 (br s, 1H), d 2.35 (s, 3H), d 3.22 (d, J=16.2 Hz, 2H), d 3.50 (d, J=16.2 Hz, 2H), d 7.15-7.30 (m, 6H), d 7.45(br d, J=7.1 Hz, 2H).

Workup

  1. stirringstirred for 3.5 h
  2. stirringAfter stirring at 0° C. for 3 h
  3. temperatureto warm to room temperature
  4. waitkept at ambient temperature overnight
  5. custom(12 h)
  6. extractionThe solution was extracted with diethyl ether (4*200 mL)
  7. washwashed with water (100 mL)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. concentrationconcentrated
  10. customto give the crude product
  11. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-ace28521be66493cae2f8b3688704dde
Source dataset
uspto-grants-1998_05
Patent number
US05747621

Reaction notes

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