p-Toluenesulfonic acid → 7-(2-thienyl)-1H-indene

HRID 1164207Notes

Reaction equation

HRID 1164207 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][CH2:9][CH:10]2O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][CH:9]=[CH:10]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 131024604-(2-Thienyl)-1-indanol

Product 1

HCID 131024627-(2-thienyl)-1H-indeneYield 96.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 2.4 g (0.011 mole) of 4-(2-thienyl)-1-indanol and 0.15 g of p-toluenesulfonic acid in 60 mL of toluene was heated under reflux, and the theoretical amount of water by-product was collected in a Dean-Stark trap. The reaction mixture was cooled and washed with two portions of 100 mL each of a 5% aqueous solution of sodium bicarbonate, then with two portions of 50 mL each of water. The organic layer was dried over magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give 2.1 g of 7-(2-thienyl)-1H-indene as an oil.

Workup

  1. temperatureunder reflux
  2. customthe theoretical amount of water by-product was collected in a Dean-Stark trap
  3. temperatureThe reaction mixture was cooled
  4. washwashed with two portions of 100 mL each of a 5% aqueous solution of sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ee9dff47e2c4fe98091600663aedb23
Source dataset
uspto-grants-1983_01
Patent number
US04368205

Reaction notes

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