Sulfuric Acid → HCID 21951266, compound

HRID 2215618Notes

Reaction equation

HRID 2215618 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[CH2:12][C:11]2[C:6](=[C:7]([CH3:25])[C:8]([CH3:24])=[C:9]([CH3:23])[C:10]=2[C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)[C:5]1=O.C1(C)C=CC=CC=1.S(=O)(=O)(O)O>CO>[CH3:3][C:4]1[CH2:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]1[CH:14]=[CH:15][C:16]([C:19]([CH3:20])([CH3:21])[CH3:22])=[CH:17][CH:18]=1)[C:9]([CH3:23])=[C:8]([CH3:24])[C:7]=2[CH3:25]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 4311764Sodium borohydrideHCID 21951279HCID 21951279, compound

Product 1

HCID 21951266HCID 21951266, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

5 g (131 mmol) of sodium borohydride and 21 g (80 mmol) of 2,5,6,7-tetramethyl-4-(4′-tert-butylphenyl)-1-indanone (3d) together with 200 ml of toluene were placed in a reaction vessel. At 50° C., 25 ml of methanol were added slowly and the reaction mixture was stirred at 50° C. for 3 hours. After cooling to room temperature, 35 ml of 2 N sulfuric acid were added and the mixture was stirred for 30 minutes. After phase separation, the organic phase was washed twice with a total of 60 ml of 2 N sulfuric acid, most of the solvent was removed and the residue was taken up in 200 ml of toluene and admixed with 0.2 g of p-toluenesulfonic acid. Water was distilled off from this reaction mixture by refluxing for 1.5 hours on a water separator until reaction was complete. The reaction mixture was washed once with 100 ml of saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. After removal of the solvent, the residue was dried in an oil pump vacuum. Crude product was purified by recrystallization in heptane. This gave 9.0 g of (3e).

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture was stirred for 30 minutes
  3. customAfter phase separation
  4. washthe organic phase was washed twice with a total of 60 ml of 2 N sulfuric acid, most of the solvent
  5. customwas removed
  6. distillationWater was distilled off from this reaction mixture
  7. temperatureby refluxing for 1.5 hours on a water separator until reaction
  8. washThe reaction mixture was washed once with 100 ml of saturated sodium hydrogen carbonate solution
  9. dry with materialdried over magnesium sulfate
  10. customAfter removal of the solvent
  11. customthe residue was dried in an oil pump vacuum
  12. customCrude product was purified by recrystallization in heptane

Sources & evidence

ORD record
ord-1864792797e345419d995d516fdb92b5
Source dataset
uspto-grants-2006_09
Patent number
US07109278B2

Reaction notes

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