p-Toluenesulfonic acid → HCID 58319207, compound

HRID 2363149Notes

Reaction equation

HRID 2363149 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2([C:13]([F:16])([F:15])[F:14])O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH:6]=[C:7]2[C:13]([F:14])([F:15])[F:16]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 58319192HCID 58319192, compound

Product 1

HCID 58319207HCID 58319207, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-methoxy-1-trifluoromethyl-indan-1-ol (170 mg, 0.73 mmol) in benzene (4 mL) was added p-toluenesulfonic acid (139 mg, 0.73 mmol). The mixture was stirred overnight at 80° C., and concentrated under reduced pressure. The crude residue was purified by column chromatography to give 4-methoxy-1-trifluoromethyl-3H-inden. The 4-methoxy-1-trifluoromethyl-3H-inden was dissolved in CH2Cl2 (2 ml) and 1M-BBr3 (in CH2Cl2, 1.46 mL, 1.46 mmol) was added dropwise. The mixture was stirred for 1 hour at room temperature, and then washed with saturated ammonium chloride, water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography to give 1-trifluoromethyl-3H-inden-4-ol (70 g, 48%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-504dfce5d5854dae9fdc8b37d04a774e
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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