Selenium Dioxide → HCID 86738419, compound

HRID 1156223Notes

Reaction equation

HRID 1156223 reaction equation
[OH:1][CH:2]([CH3:20])[CH2:3][O:4][C:5]1[C:10]2C(=O)C=C(C)O[C:9]=2[C:8](CCC)=[CH:7][CH:6]=1.[Se](=O)=[O:22].[O:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[OH:1][CH:2]([CH3:20])[CH2:3][O:4][C:5]1[CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:25][C:26]=2[O:27][C:28]=1[C:29]([OH:24])=[O:22]

Participants

4

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 53892944HCID 53892944, compound

Product 1

HCID 86738419HCID 86738419, compound

Procedure

5 -(2-Hydroxypropoxy)-2-methyl-4-oxo-8-propyl-4H-1-benzopyran (2.6 g) and selenium dioxide (1.1 g) were dissolved in 20% aqueous dioxan (150 ml) and heated at reflux for 24 hours. The suspension was filtered and the dioxan removed in vacuo. The residue was dissolved in chloroform (100 ml) and the chloroform solution extracted with saturated aqueous sodium bicarbonate. The bicarbonate extract was acidified with dilute hydrochloric acid and the resulting precipitate filtered off, washed with water and dried. Crystallisation from acetone gave 5-(2-hydroxypropoxy-4H-1-benzopyran-2-carboxylic acid. mp 135°-137° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. filtrationThe suspension was filtered
  4. customthe dioxan removed in vacuo
  5. dissolutionThe residue was dissolved in chloroform (100 ml)
  6. extractionthe chloroform solution extracted with saturated aqueous sodium bicarbonate
  7. extractionThe bicarbonate extract
  8. filtrationthe resulting precipitate filtered off
  9. washwashed with water
  10. customdried
  11. customCrystallisation from acetone

Sources & evidence

ORD record
ord-28625806f45848b19d2cd1bbd2cb8cd1
Source dataset
uspto-grants-1982_06
Patent number
US04335048

Reaction notes

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