Hydrochloric Acid → 4-(4-Tert-butylphenyl)-6-methyl-1,2,3,5-tetrahydro-s-indacene

HRID 271793Notes

Reaction equation

HRID 271793 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:22]3[CH2:21][CH2:20][CH2:19][C:18]=3[CH:17]=[C:16]3[C:12]=2[CH2:13][CH:14]([CH3:24])[C:15]3=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C(OCC)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]3[CH2:13][C:14]([CH3:24])=[CH:15][C:16]=3[CH:17]=[C:18]3[C:22]=2[CH2:21][CH2:20][CH2:19]3)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 687458344-(4-tert-butylphenyl)-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

Product 1

HCID 860499404-(4-Tert-butylphenyl)-6-methyl-1,2,3,5-tetrahydro-s-indacene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

10 g (0.031 mol) of 4-(4-tert-butylphenyl)-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one (1c) were added dropwise at 0° C. to a solution of 0.6 g (0.016 mol) of lithium aluminum hydride in 100 ml of diethyl ether. The reaction mixture obtained was warmed to room temperature and stirred for a further one hour. 50 ml of 5% strength hydrochloric acid were added. The organic phase was separated off, washed twice with water and dried over magnesium sulfate. The residue was dissolved in 200 ml of benzene and, after addition of 0.5 g of p-toluenesulfonic acid, refluxed for 15 minutes. The solution was cooled to room temperature, washed with a 5% strength solution of sodium hydrogencarbonate and dried over magnesium sulfate. Evaporation of the solvent gave pure 4-(4-tert-butylphenyl)-6-methyl-1,2,3,5-tetrahydro-s-indacene in quantitative yield.

Workup

  1. customThe reaction mixture obtained
  2. customThe organic phase was separated off
  3. washwashed twice with water
  4. dry with materialdried over magnesium sulfate
  5. dissolutionThe residue was dissolved in 200 ml of benzene
  6. additionafter addition of 0.5 g of p-toluenesulfonic acid
  7. temperaturerefluxed for 15 minutes
  8. temperatureThe solution was cooled to room temperature
  9. washwashed with a 5% strength solution of sodium hydrogencarbonate
  10. dry with materialdried over magnesium sulfate
  11. customEvaporation of the solvent

Sources & evidence

ORD record
ord-45f98f5d127946ccbd1267387df33177
Source dataset
uspto-grants-2008_11
Patent number
US07452949B2

Reaction notes

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