Potassium Hydroxide → HCID 13046230, compound

HRID 1759463Notes

Reaction equation

HRID 1759463 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:5]=1[O:6][CH2:7]/[CH:8]=[C:9](\[CH3:14])/[C:10]([O:12]C)=[O:11]>O1CCCC1CO>[Cl:3][C:4]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:5]=1[O:6][CH2:7]/[CH:8]=[C:9](\[CH3:14])/[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13046227HCID 13046227, compound

Product 1

HCID 13046230HCID 13046230, compound

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

In 20 ml of a 1:1 tetrahydrofuran-methanol mixture 0.38 g methyl (E)-4(2,4-dichlorophenoxy)-2-methyl-2-buten-1-oate is dissolved and the solution stirred under nitrogen as a 20% aqueous potassium hydroxide solution is added dropwise. The solution is then heated at reflux for about 2 hours before being evaporated to dryness. The residue is taken up in 20 ml water and filtered to remove the very small amount of insoluble material and is then acidified with dropwise addition of dilute aqueous HCl. The mixture is extracted with two 20 ml portions of methylene chloride and the extracts are combined and treated with magnesium sulfate and the mixture filtered. The filtrate is heated under a stream of nitrogen as 5 ml of hexane is added. When the volume reaches 10 ml the solution is allowed to cool to room temperature and is placed in a freezer. A white needle-like crystalline solid forms and is collected by nitrogen pressure filtration and after drying on the filter 0.11 g solid product is collected, m.p. 117°- 121.5° C.

Workup

  1. additionis added dropwise
  2. temperatureThe solution is then heated
  3. temperatureat reflux for about 2 hours
  4. custombefore being evaporated to dryness
  5. filtrationfiltered
  6. customto remove the very small amount of insoluble material
  7. additionis then acidified with dropwise addition of dilute aqueous HCl
  8. extractionThe mixture is extracted with two 20 ml portions of methylene chloride
  9. additiontreated with magnesium sulfate
  10. filtrationthe mixture filtered
  11. temperatureThe filtrate is heated under a stream of nitrogen as 5 ml of hexane
  12. additionis added
  13. filtrationA white needle-like crystalline solid forms and is collected by nitrogen pressure filtration
  14. dry with materialafter drying on the filter 0.11 g solid product
  15. customis collected

Sources & evidence

ORD record
ord-5da5a00d555c4e46b9e649c63f037a95
Source dataset
uspto-grants-1982_07
Patent number
US04340765

Reaction notes

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