Water → 4-Benzoyl-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 436178Notes

Reaction equation

HRID 436178 reaction equation
[O:1]1CCOCC1.[CH2:7]([C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][CH2:17][CH:18]2[C:23]([OH:25])=[O:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Se](=O)=O.O>C(Cl)(Cl)Cl>[C:7]([C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][CH2:17][CH:18]2[C:23]([OH:25])=[O:24])(=[O:1])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 12422114HCID 12422114, compound

Product 1

HCID 1621494-Benzoyl-2,3-dihydro-1H-indene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 60 ml. of dioxane are added 6.3 g. of 4-benzylindan-1-carboxylic acid and 2.8 g. of selenium dioxide and the mixture is refluxed for 12 hours. After cooling, water and chloroform are added and the insolubles are filtered off. The filtrate is extracted with chloroform and the chloroform layer is extracted with 5 % aqueous potassium carbonate. The extract is decolorized with activated carbon and rendered acidic with hydrochloride acid. The precipitate is extracted with chloroform and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is crystallized from a 20:7 solvent mixture of cyclohexane and benzene. The described procedure gives 4-benzoylindan-1-carboxylic acid as crystals melting at 100°-102° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe insolubles are filtered off
  3. extractionThe filtrate is extracted with chloroform
  4. extractionthe chloroform layer is extracted with 5 % aqueous potassium carbonate
  5. extractionThe precipitate is extracted with chloroform
  6. washthe extract is washed with water
  7. customdried
  8. distillationThe solvent is distilled off under reduced pressure
  9. customthe residue is crystallized from a 20:7 solvent mixture of cyclohexane and benzene

Sources & evidence

ORD record
ord-a90b554921e34d89a3710174468b6814
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

Loading…