Sulfuric Acid → HCID 58444098, compound

HRID 1965828Notes

Reaction equation

HRID 1965828 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][CH:14]([CH2:21][C:22]2([CH3:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:15]3=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C1(C)C=CC=CC=1.OS(O)(=O)=O>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][C:14]([CH2:21][C:22]2([CH3:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)=[CH:15]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 4311764Sodium borohydride2×HCID 58444081HCID 58444081, compound

Product 1

HCID 58444098HCID 58444098, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

27.9 g of crude 4-(4-tert-butyl-phenyl)-2-[(1-methylcyclohexyl)methyl]-indan-1-one (˜83% purity), 2.82 g (74.5 mmol) of NaBH4 and 70.5 ml of toluene are charged in a flask equipped with reflux condenser, dropping funnel and magnetic stirring bar. The mixture is warmed to 50° C. and 14 ml of methanol are slowly added with stirring and stirring is continued for 2.5 h to ensure a complete reaction. Excess NaBH4 is carefully hydrolyzed with approx. 40 ml of 2n H2SO4. The organic phase is separated and the water phase is washed with another 35 ml of toluene. The combined organic phases are twice extracted with 2n H2SO4 and dried over anhydrous MgSO4. Most of the solvent is removed in a vacuum and replaced by fresh toluene up to a total volume of 100 ml and 0.3 g of p-toluenesulfonic acid are added. The reaction flask is fitted with a water separator and the reaction mixture is heated to reflux for 1.5 h. The conversion can be monitored by TLC. Once the dehydration is complete, the solution is washed with a saturated NaHCO3 solution and dried over anhydrous MgSO4. The solvent is thoroughly removed in a vacuum and 25.85 g of a brown oil is obtained. Purification of the indene is carried out via a column chromatography. Yield: 18.85 g (˜85%) of 7-(4-tert-Butyl-phenyl)-2-[(1-methylcyclohexyl)methyl]-1H-indene.

Workup

  1. customequipped
  2. temperaturewith reflux condenser
  3. stirringstirring
  4. customa complete reaction
  5. customThe organic phase is separated
  6. washthe water phase is washed with another 35 ml of toluene
  7. extractionThe combined organic phases are twice extracted with 2n H2SO4
  8. dry with materialdried over anhydrous MgSO4
  9. customMost of the solvent is removed in a vacuum
  10. additionare added
  11. customThe reaction flask is fitted with a water separator
  12. temperaturethe reaction mixture is heated
  13. temperatureto reflux for 1.5 h
  14. washthe solution is washed with a saturated NaHCO3 solution
  15. dry with materialdried over anhydrous MgSO4
  16. customThe solvent is thoroughly removed in a vacuum

Sources & evidence

ORD record
ord-0aed6115460f4afea45cf1eb37ad1e87
Source dataset
uspto-grants-2013_04
Patent number
US08415492B2

Reaction notes

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