Sodium Hydroxide → 2-[4-(Oxan-4-yl)phenoxy]propanoic acid

HRID 1678974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678974
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH:12]([CH3:18])[C:13]([O:15]CC)=[O:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH:12]([CH3:18])[C:13]([OH:15])=[O:14])=[CH:19][CH:20]=2)[CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22765982Ethyl 2-[4-(oxan-4-yl)phenoxy]propanoate

Produkt 1

HCID 203654662-[4-(Oxan-4-yl)phenoxy]propanoic acidAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

7.6 g of ethyl 2-[p-(4-tetrahydropyranyl)-phenoxy]-propanoate were added to a solution of 17 ml of 2N sodium hydroxide and 100 ml of ethanol and the mixture was stirred for 2 hours at room temperature and then was refluxed for 30 minutes. The mixture was evaporated to dryness and the residue was dissolved in 20 ml of N sodium hydroxide. The solution was washed with ether and acidified with 4N hydrochloric acid. The mixture was filtered and the recovered crystals were washed with water and dried. The product was crystallized from a 50-50 cyclohexane-ethyl acetate mixture to obtain 6.1 g of 2-[p-(4-tetrahydropyranyl)-phenoxy]-propanoic acid melting at 156° C.

Aufarbeitung

  1. temperaturewas refluxed for 30 minutes
  2. customThe mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in 20 ml of N sodium hydroxide
  4. washThe solution was washed with ether
  5. filtrationThe mixture was filtered
  6. washthe recovered crystals were washed with water
  7. customdried
  8. customThe product was crystallized from a 50-50 cyclohexane-ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-03cd5983ed1f4051a3b5dd1ff1f062f2
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04078076

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