2-Indanone → 2-Indanone

HRID 1872301Notes

Reaction equation

HRID 1872301 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[C:5]1([CH3:13])[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Mg]Br.[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][CH:8]=[CH:7][C:6]=1[C:15]1([OH:23])[CH2:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14]1

Participants

6

Reactant 3

HCID 119832-IndanoneHCID 24636Cerium(III) chlorideHCID 178424303HCID 178424303, compound

Product 2

HCID 119832-IndanoneHCID 18690313HCID 18690313, 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. o-Tolylmagnesium bromide (70.0 mL of 2.0 M solution in diethyl ether, 140.0 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 (120° C./0.3 mm Hg) yielded 4.0 g of 2-indanone and 10.38 g of 2-(o-tolyl)-2-indanol in solid form. 1H-N.M.R. (CDCl3) d 2.13 (br s, 1H), d 2.52(s, 3H), d 3.36 (d, J=16.2 Hz, 2H), d 3.63 (d, J=16.2 Hz, 2H), d 7.15-7.62 (m, 8H)

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 (120° C./0.3 mm Hg)

Sources & evidence

ORD record
ord-2eb80c7c544c43858faf2d79b38bca1b
Source dataset
uspto-grants-2000_08
Patent number
US06107431

Reaction notes

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