Hydrochloric Acid → 2-Phenyl-1H-indene

HRID 413498Notes

Reaction equation

HRID 413498 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.Cl>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:11]1([C:2]2[CH2:3][C:4]3[C:9]([CH:1]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 119832-IndanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 3534352-Phenyl-1H-indeneYield 64.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent2×

Procedure

A solution of 2-indanone (13.47 g, 102 mmol) in anhydrous benzene (100 mL) is added to phenylmagnesium bromide (3.0 M in diethyl ether, 50.9 mL, 153 mmol) at 5° C. over 2.5 hours. The reaction was allowed to warm to room temperature over 30 minutes. The solution was cooled to 0° C. and 150 mL of water are added. The resultant mixture was diluted with 200 mL of hexanes, neutralized with 5 M HCl, and washed with brine (2×100 mL). The aqueous layer was extracted with hexanes (2×50 mL), and the combined organic layers were dried (MgSO4), filtered, and the solvent removed in vacuo from the filtrate to yield a brown oil. This oil and p-toluenesulfonic acid (0.50 g) were dissolved in benzene (250 mL) in a round-bottom flask below a Soxhlet extractor containing 4 Å molecular sieves. After refluxing for 2.5 hours, the solution was filtered and cooled to 5° C. overnight. The product, a white flaky solid, was collected by filtration, and was washed with 50 mL of cold benezene. Additional product is obtained by concentrating the filtrate, cooling, and filtering the crystals (12.60 g, 64.3% yield). 1H NMR (400 Mhz, 20° C., CDCl3)δ7.62 (d, J=7.3 Hz, 2H), 7.47 (d, J=7.3 Hz, 1H), 7.39 (M, 3H), 7.27 (m, 2H), 7.22 (s,1H), 7.18 (t, J=7.4 Hz, 1H), 3.78 (S<2H). 13C{1H} NMR (100 Mhz, 20° C., CDCl3): δ146.3, 145.3, 143.1, 135.9, 128.6, 127.5, 126.5, 126.4, 125.6, 124.7, 123.6, 120.9, 38.9.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. washwashed with brine (2×100 mL)
  3. extractionThe aqueous layer was extracted with hexanes (2×50 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo from the filtrate
  7. customto yield a brown oil
  8. additioncontaining 4 Å molecular sieves
  9. temperatureAfter refluxing for 2.5 hours
  10. filtrationthe solution was filtered
  11. temperaturecooled to 5° C. overnight
  12. filtrationThe product, a white flaky solid, was collected by filtration
  13. washwas washed with 50 mL of cold benezene
  14. customAdditional product is obtained
  15. concentrationby concentrating the filtrate
  16. temperaturecooling

Sources & evidence

ORD record
ord-9a3e96799b1740ed99fcbd6b7efc53dd
Source dataset
uspto-grants-2003_05
Patent number
US06566544B1

Reaction notes

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