Sodium Iodide → 5-(2-Formyl-3-methoxyphenoxy)pentanoic acid

HRID 647894

Reaktionsgleichung

Reaktionsgleichung von HRID 647894
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].BrC[CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18].[C:22](=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[CH:4]([C:3]1[C:2]([O:1][CH3:22])=[CH:9][CH:8]=[CH:7][C:6]=1[O:10][CH2:11][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:5]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 696926-MethoxysalicylaldehydeHCID 84580Ethyl 5-bromovalerate

Produkt 1

HCID 204843395-(2-Formyl-3-methoxyphenoxy)pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Hydroxy-6-methoxybenzaldehyde (16.875 g., 0.111 M), ethyl 5-bromopentanoate (23.25 g., 17.6 ml., 0.111 M), anhydrous potassium carbonate (16.5 g.), sodium iodide (0.675 g.) and 95% ethanol (150 ml.) were refluxed with stirring (16 hrs). The cooled reaction mixture was filtered and the solid washed well with ethanol. The filtrate was evaporated to dryness and the residue partitioned between ether and water. The ethereal layer was separated and washed with 2 N sodium hydroxide solution, water, dried (sodium sulphate) and evaporated. The residue was dissolved in 95% ethanol (300 ml.) and 0.66 N sodium hydroxide solution (450 ml.) and stirred at ambient temperature (4 hrs). The reaction mixture was evaporated to half volume and diluted with water. The mixture was extracted once with ether and the aqueous layer acidified with concentrated hydrochloric acid with cooling. The crystalline solid formed was filtered off and washed well with water. Recrystallisation from ethyl acetate-petrol gave 5-(2-formyl-3-methoxyphenoxy)pentanoic acid, m.p. 99°-101° C. (Found: C, 61.98; H, 6.58. C13H16O5 requires C, 61.89; H, 6.39%).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. washthe solid washed well with ethanol
  4. customThe filtrate was evaporated to dryness
  5. customthe residue partitioned between ether and water
  6. customThe ethereal layer was separated
  7. washwashed with 2 N sodium hydroxide solution, water
  8. dry with materialdried (sodium sulphate)
  9. customevaporated
  10. dissolutionThe residue was dissolved in 95% ethanol (300 ml.)
  11. stirring0.66 N sodium hydroxide solution (450 ml.) and stirred at ambient temperature (4 hrs)
  12. customThe reaction mixture was evaporated to half volume
  13. additiondiluted with water
  14. extractionThe mixture was extracted once with ether
  15. temperaturewith cooling
  16. customThe crystalline solid formed
  17. filtrationwas filtered off
  18. washwashed well with water
  19. customRecrystallisation from ethyl acetate-petrol

Quellen und Nachweise

ORD-Eintrag
ord-b9e9f61a990a43eeb95ac4522d7ce523
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04410537

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