2-Indanone → HCID 18690302, compound

HRID 1289273Notes

Reaction equation

HRID 1289273 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[C:5]([C:9]1[CH:14]=[CH:13][C:12]([Mg]Br)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].[CH2:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C:18]1=[O:26]>C1COCC1>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([C:18]2([OH:26])[CH2:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17]2)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 119832-IndanoneHCID 24636Cerium(III) chlorideHCID 178440986HCID 178440986, compound

Product 1

HCID 18690302HCID 18690302, compoundYield 81.7%

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. 4-t-Butylphenylmagnesium bromide (70.0 mL of 2.0M 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. 2-Indanone (1.34 g) was distilled off at 80° C/0.3 mm Hg. The residue was washed with pentane (50 mL) and subject to Kugelrohr distillation (185° C./0.3 mm Hg). 2-(4-t-Butyl-phenyl)-2-indanol (23.43 g) was obtained in pure form. 1H-N.M.R. (CDCl3) d 1.32 ( s, 9H), d 1.36 (s, 1H), d 3.25 (d, J=16.2 Hz, 2H), d 3.50 (d, J=16.2 Hz, 2H), d 7.15-7.45 (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. distillation2-Indanone (1.34 g) was distilled off at 80° C/0.3 mm Hg
  12. washThe residue was washed with pentane (50 mL)
  13. distillationsubject to Kugelrohr distillation (185° C./0.3 mm Hg)

Sources & evidence

ORD record
ord-b9a8b5d6183d4ca1a899bd76c68910a9
Source dataset
uspto-grants-1998_05
Patent number
US05747621

Reaction notes

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