Toluene → 5,6-dichloro-1H-indene

HRID 2226533Notes

Reaction equation

HRID 2226533 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[CH:7](O)[CH2:6][CH2:5]2.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>O.C(C1C=C(O)C(=CC=1)O)(C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[CH2:7][CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 199195245,6-Dichloro-2,3-dihydro-1H-inden-1-OL

Product 1

HCID 199195275,6-dichloro-1H-indeneYield 56.5%

Reagents, catalysts & solvents 2

HCID 73814-tert-ButylcatecholCatalystHCID 962WaterSolvent

Procedure

A mixture of 17.48 g of the product of Step B, 470 ml of toluene, 0.57 g of 4-tert.-butyl-catechol and 1.63 g of p-toluene sulfonic acid was refluxed for 2 hours and then was diluted with water. 10 ml of N sodium hydroxide solution were added and the mixture was extracted with toluene. The organic phase was evaporated to dryness under reduced pressure and the residue was taken up in hexane. The mixture was vacuum filtered and the crystalline product was dried to obtain 9 g of the desired product melting at 76° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionthe mixture was extracted with toluene
  3. customThe organic phase was evaporated to dryness under reduced pressure
  4. filtrationfiltered
  5. customthe crystalline product was dried

Sources & evidence

ORD record
ord-697626cccf67485283f663d344ef5127
Source dataset
uspto-grants-1994_09
Patent number
US05348971

Reaction notes

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