Bromoform → 2-Methoxy-2-(4-morpholinophenyl)acetic acid

HRID 56486

Reaktionsgleichung

Reaktionsgleichung von HRID 56486
[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-:15].[K+].[CH:17](Br)(Br)Br.[OH-:21].[K+].[CH3:23][OH:24]>CO.O1CCOCC1>[CH3:17][O:15][CH:11]([C:10]1[CH:13]=[CH:14][C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:8][CH:9]=1)[C:23]([OH:24])=[O:21]

Komponenten

7

Edukt 4

HCID 5558BromoformHCID 14797Potassium HydroxideHCID 2913494-MorpholinobenzaldehydeHCID 23689386Potassium hydroxide methanol

Produkt 1

HCID 584321092-Methoxy-2-(4-morpholinophenyl)acetic acidAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

An oven-dried flask was charged with 4-(4-morpholinyl)benzaldehyde (10.1 g, 53 mmol), anhydrous methanol (60 mL) and anhydrous dioxane (60 mL) then fitted with an addition funnel. The addition funnel was charged with a solution of KOH (14.8 g, 264 mmol) in anhydrous methanol (60 mL) and an aliquot (˜2 mL) was added to the reaction mixture. Bromoform (5.8 mL, 67.1 mmol) was added to the reaction mixture then the remaining KOH/MeOH solution was added dropwise over 10 minutes. After stirring for 18 h, the mixture was filtered through Celite and rinsed with methanol. The filtrate was collected and concentrated in vacuo. The residue was then diluted with saturated aqueous NH4Cl and extracted with EtOAc. Additional EtOAc was then used to extract the aqueous phase while slowly adjusting the pH from ˜8 to ˜2 using concentrated HCl. A total of approximately 1.5 L of EtOAc was used for the extraction process. The combined EtOAc extracts were dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo gave 2-methoxy-2-(4-morpholinophenyl)acetic acid as a tan solid (7.25 g, 58%).

Aufarbeitung

  1. customthen fitted with an addition funnel
  2. additionan aliquot (˜2 mL) was added to the reaction mixture
  3. filtrationthe mixture was filtered through Celite
  4. washrinsed with methanol
  5. customThe filtrate was collected
  6. concentrationconcentrated in vacuo
  7. additionThe residue was then diluted with saturated aqueous NH4Cl
  8. extractionextracted with EtOAc
  9. extractionto extract the aqueous phase
  10. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-1e52a94da63c4f9db6dad8d67985954b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434707B2

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