p-Toluenesulfonic acid monohydrate → 2,4,7-trimethyl-1H-indene

HRID 2425310Notes

Reaction equation

HRID 2425310 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=2[CH3:11])[CH:3]1O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=2[CH3:11]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22463177HCID 22463177, compound

Product 1

HCID 110626602,4,7-trimethyl-1H-indeneYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9.06 g of 2,4,7 trimethylindanol (51.4 mmol) were dissolved in 100 ml of toluene in a 250 ml, 2-neck flask equipped with magnetic stirring bar, Dean-Stark separator and bubble condenser. 0.15 g of p-toluenesulphonic acid monohydrate (0.78 mmol, 0.015 eq) were added, and the solution was heated to reflux, distilling the toluene-H2O azeotrope. After about 2 h, the temperature increased toward the boiling point of toluene, and after a few drops of pure toluene distillate, the reaction was stopped by cooling to room temperature and treating the solution with 100 ml of saturated NaHCO3 aqueous solution. The organic phase was extracted with Et2O with the standard procedure, the combined organic phases were washed with H2O and then dried with Na2SO4. After filtration, the solvents were evaporated under reduced pressure to give 7.24 g of an off-white waxy product (yield: 89%).

Workup

  1. customequipped with magnetic stirring bar
  2. customDean-Stark separator and bubble condenser
  3. temperaturethe solution was heated
  4. temperatureto reflux
  5. distillationdistilling the toluene-H2O azeotrope
  6. temperaturethe temperature increased toward the boiling point of toluene
  7. additiontreating the solution with 100 ml of saturated NaHCO3 aqueous solution
  8. extractionThe organic phase was extracted with Et2O with the standard procedure
  9. washthe combined organic phases were washed with H2O
  10. dry with materialdried with Na2SO4
  11. filtrationAfter filtration
  12. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-e0f194202d414559944ca0229f11c5ba
Source dataset
uspto-grants-2011_06
Patent number
US07964679B2

Reaction notes

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