Hydrochloric Acid → 2-Methyl-7-phenylindene

HRID 1106957Notes

Reaction equation

HRID 1106957 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]1=O.[BH4-].[Na+].Cl>C1COCC1.CO>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][C:8]=2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 42924012-Methyl-4-phenyl-2,3-dihydro-1H-inden-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 42924022-Methyl-7-phenylindene

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

50 g (0,226 mol) of 2 were dissolved in 450 cm3 of THF/MeOH (2:1) and, while stirring at 0° C., 12.8 g (0.34 mol) of sodium borohydride were added a little at a time. The mixture was stirred for a further 18 hours. The reaction mixture was poured onto ice, acidified with concentrated HCl to a pH of 1 and extracted a number of times with Et2O. The combined organic phases were washed with saturated aqueous NaHCO3 solution and NaCl solution and then dried (MgSO4). The solvent was removed under reduced pressure and the crude product was, without further purification, taken up in 1 dm3 of toluene, admixed with 2 g of p-toluenesulfonic acid and heated under reflux for 2 hours. The reaction mixture was washed with 200 cm3 of saturated aqueous NaHCO3 solution and the solvent was removed under reduced pressure. The crude product was purified by filtration through 500 g of silica gel (hexane/CH2Cl2). This gave 42 g (90%) of 3 as a colorless oil.

Workup

  1. stirringThe mixture was stirred for a further 18 hours
  2. additionThe reaction mixture was poured onto ice
  3. extractionextracted a number of times with Et2O
  4. washThe combined organic phases were washed with saturated aqueous NaHCO3 solution and NaCl solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe crude product was, without further purification
  8. temperatureheated
  9. temperatureunder reflux for 2 hours
  10. washThe reaction mixture was washed with 200 cm3 of saturated aqueous NaHCO3 solution
  11. customthe solvent was removed under reduced pressure
  12. filtrationThe crude product was purified by filtration through 500 g of silica gel (hexane/CH2Cl2)

Sources & evidence

ORD record
ord-403b24513cee4571932a8dc1d6fe127f
Source dataset
uspto-grants-2000_05
Patent number
US06057408

Reaction notes

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