2-Indanone → HCID 14449200, compound

HRID 1289269Notes

Reaction equation

HRID 1289269 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[C:5]1([Mg]Br)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C:14]1=[O:22]>C1COCC1>[C:5]1([C:14]2([OH:22])[CH2:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 119832-IndanoneHCID 24636Cerium(III) chlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 14449200HCID 14449200, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of anhydrous cerium chloride (40.60 g, 164.7 mmol) in THF (270 mL) was stirred at room temperature for 2 hours under nitrogen. Phenylmagnesium bromide (46.5 mL of 3.0M solution in diethyl ether, 139.5 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 hours, the mixture was allowed to warm to room temperature and kept at ambient temperature for 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 (150° C./0.25 mm Hg yielded 18.58 g (82%) of 2-phenyl-2-indanol in solid form (mp 54°C.). 1H-N.M.R. (CDCl3) d 2.24 (br s, 1H), d 3.20 (d, J=16.2 Hz, 2H), d 3.43 (d, J=16.2 Hz, 2H), d 7.18-7.40 (m, 7H), d 7.51(br d, J=7.1 Hz, 2H)

Workup

  1. stirringstirred for 3.5 h
  2. stirringAfter stirring at 0° C. for 3 hours
  3. temperatureto warm to room temperature
  4. waitkept at ambient temperature for 12 h
  5. extractionThe solution was extracted with diethyl ether (4*200 mL)
  6. washwashed with water (100 mL)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-006f820b2a7c46b4bb26595fac1a8cd9
Source dataset
uspto-grants-1998_05
Patent number
US05747621

Reaction notes

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