Selenium Dioxide → HCID 13059696, compound

HRID 1606737Notes

Reaction equation

HRID 1606737 reaction equation
[O:1]1CCOCC1.[CH3:7][O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH2:17][CH:18]3[C:23]#[N:24])=[CH:11][CH:10]=1.[Se](=O)=O>O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][CH2:17][CH:18]3[C:23]#[N:24])=[O:1])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 20310112HCID 20310112, compound

Product 1

HCID 13059696HCID 13059696, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 60 ml. of dioxane are added 8.0 g. of 4-(p-methoxybenzyl)indan-1-carbonitrile and 2.8 g. of selenium dioxide and the mixture is refluxed for 12 hours. After cooling, water is added, followed by extraction with chloroform. The extract is washed with water and dried. Then, the solvent is distilled off under reduced pressure and the residue is purified by column chromatography (500 g. silica gel; eluted with chloroform). The crude crystals thus obtained are recrystallized from benzene. The procedure gives 4-(p-methoxybenzoyl)indan-1-carbonitrile as crystals melting at 115.5°-117.5°C.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with chloroform
  3. washThe extract is washed with water
  4. customdried
  5. distillationThen, the solvent is distilled off under reduced pressure
  6. customthe residue is purified by column chromatography (500 g. silica gel; eluted with chloroform)
  7. customThe crude crystals thus obtained
  8. customare recrystallized from benzene

Sources & evidence

ORD record
ord-450d9e128f464b76a8c32a3a84a68f95
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

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