p-Toluenesulfonic acid monohydrate → 5-methyl-1H-indene

HRID 501908Notes

Reaction equation

HRID 501908 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2O)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][CH:7]=[CH:8]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 123372176-Methyl-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 819975-methyl-1H-indene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium borohydride (1.3 g) was added to a solution of 6-methyl-indane-1-one (5.0 g) in methanol (50 ml) at 0° C., and the mixture was stirred for one hour. The reaction mixture was poured into ice-cooled water, and extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain 6-methylindane-1-ol (5.5 g). To a solution of 6-methylindane-1-ol in toluene (50 ml) was added p-toluene sulfonic acid monohydrate (0.2 g), and the mixture was stirred for 20 minutes. The temperature of the reaction mixture was returned to room temperature, and the reaction mixture was washed with water, 5% sodium hydrogencarbonate aqueous solution, and saturated saline solution in order and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain 5-methyl-1H-indene (5.5 g).

Workup

  1. customwas returned to room temperature
  2. washthe reaction mixture was washed with water, 5% sodium hydrogencarbonate aqueous solution, and saturated saline solution in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bba1f53cb36c49f8ae1af80aa32433b7
Source dataset
uspto-grants-2010_08
Patent number
US07772407B2

Reaction notes

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