Water → 1H-Indene, 2-(1-methylethyl)-4-phenyl-

HRID 842582Notes

Reaction equation

HRID 842582 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].O.[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH:1]([C:2]1[CH2:11][C:1]2[C:6]([CH:3]=1)=[C:5]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH:4]=[CH:3][CH:2]=2)([CH3:11])[CH3:6]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 180082381H-Indene, 2-(1-methylethyl)-4-phenyl-

Procedure

The crude mix of isomeric alcohols was dissolved in toluene (150 ml) to which p-toluene sulfonic acid (0.5 g) was added. The solution was refluxed in a flask equipped with a Dean-Stark trap for 1.5 h then cooled. Solid sodium bicarbonate was added and the mixture was stored overnight in a refrigerator. The next morning water (100 ml) was added and the organic layer was separated, dried over Na2SO4, and stripped under reduced pressure. The product, 2-isopropyl-4-phenylindene (10.4 g) was obtained as a brown oil. Analysis by GC indicated a purity of >96 area percent. This material was stored cold under an inert atmosphere until ready for further conversion.

Workup

  1. additionwas added
  2. temperatureThe solution was refluxed in a flask
  3. customequipped with a Dean-Stark trap for 1.5 h
  4. temperaturethen cooled
  5. customthe organic layer was separated
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-7aa0c48b05e5462c9e64cdce3b61014a
Source dataset
uspto-grants-2002_04
Patent number
US06376406B1

Reaction notes

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