Hydrochloric Acid → 4,7-dimethyl-1H-indene

HRID 321917Notes

Reaction equation

HRID 321917 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl.CC1C=CC(C)=C2C=1CCC2O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(OCC)C.C1COCC1>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 24436Sodium SulfateHCID 2200944,7-Dimethyl-1-indanone2×HCID 516892Sodium BicarbonateHCID 158776054,7-Dimethyl-1-indanolHCID 21226445Aluminium lithium hydride

Product 1

HCID 814584,7-dimethyl-1H-indeneYield 91.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

2.9 g (0.0181 moles) of 4,7-dimethyl-1-indanone (formula XVII) obtained as described above, are slowly added to a suspension of 0.350 g (0.0692 moles) of LiAlH4 in 30 ml of ethyl ether, maintained at −30° C. in an inert atmosphere. The reaction is complete after 30 minutes. Ice and HCl 2N are cautiously added until acidification, the mixture is then extracted with ethyl ether, and the organic phase is subsequently separated and washed until neutrality. It is anhydrified on sodium sulfate and evaporated, obtaining a residue essentially consisting of 4,7-dimethyl-1-indanol. The residue is dissolved in 10 ml of THF, a pinch of p-toluenesulfonic acid is added and the mixture is brought to reflux temperature for 1 hour. Solid NaHCO3 and Na2SO4 are then added. The mixture is filtered and the solvent evaporated obtaining 2.4 g of 4,7-dimethylindene (XVIII) (91% yield).

Workup

  1. extractionthe mixture is then extracted with ethyl ether
  2. customthe organic phase is subsequently separated
  3. washwashed until neutrality
  4. customevaporated
  5. customobtaining a residue
  6. temperatureto reflux temperature for 1 hour
  7. filtrationThe mixture is filtered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-0aa9780815a7402c8577ecf3c21be3fa
Source dataset
uspto-grants-2001_04
Patent number
US06211110B1

Reaction notes

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