Selenium Dioxide → HCID 20351772, compound

HRID 328680Notes

Reaction equation

HRID 328680 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:16][OH:17])=[C:6]([CH:15]=1)[CH:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Se](=O)=O>C(O)(=O)C>[C:7]([C:6]1[CH:15]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[CH:16]=[O:17])(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 12241058HCID 12241058, compound

Product 1

HCID 20351772HCID 20351772, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 9.3 g. of 5-chloro-2-hydroxymethylbenzhydrol in 50 ml. of acetic acid and 5.2 g. of selenium dioxide was refluxed for 3 hours. The mixture was filtered, cooled, poured on ice, made alkaline and extracted with ether. Concentration and addition of petroleum ether gave the product as prisms which after recrystallization from a mixture of ether and petroleum ether melted at 82°-84°. Ultraviolet maxima (2-propanol) at 230 μ (ε = 19,500) and 257 μ (ε = 23,500); infrared absorption (CHCl3) at 1675 cm-1 and 1705 cm-1.

Workup

  1. filtrationThe mixture was filtered
  2. temperaturecooled
  3. additionpoured on ice
  4. extractionextracted with ether
  5. concentrationConcentration and addition of petroleum ether

Sources & evidence

ORD record
ord-45bf9c05886143bf83f9886bc1cf0bdf
Source dataset
uspto-grants-1977_04
Patent number
US04018765

Reaction notes

Loading…