Hydroquinone → 1H-Indene, 2-methyl-

HRID 375649

Reaction equation

HRID 375649 reaction equation
[CH3:1][C:2]1(O)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O.O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 5692202-Methyl-2-indanol

Product 1

HCID 165871H-Indene, 2-methyl-Yield 81.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-2-indanol (66.2 g) was dissolved in toluene (500 ml) in a 1 liter flask equipped with a Dean-Stark trap. To this solution p-toluene sulfonic acid (2 g) and a small amount of hydroquinone were added, and the mixture was refluxed for 2.5 hours. After 8 ml of H2O was generated, the reaction mixture was cooled to 0° C. and H2O (1 liter), also cooled to 03C, was added. The organic phase was separated and washed three times with water (500 ml). The toluene was evaporated and the residue (with trace of hydroquinone added) was distilled at reduced pressure to give 2-methylindene (47.2 g, 48%) as clear slightly green liquid.

Workup

  1. customequipped with a Dean-Stark trap
  2. temperaturethe mixture was refluxed for 2.5 hours
  3. additionwas added
  4. customThe organic phase was separated
  5. washwashed three times with water (500 ml)
  6. customThe toluene was evaporated
  7. additionthe residue (with trace of hydroquinone added)
  8. distillationwas distilled at reduced pressure

Sources & evidence

ORD record
ord-816469b7869b4c86ada6e459380a76a4
Source dataset
uspto-grants-1996_01
Patent number
US05486585

Linked notes

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