Methanol → 3-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid

HRID 1524267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524267
[OH-].[Li+].C[O:4][C:5](=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14](=[O:24])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[CH:7]=1.CO.O1CCCC1>O>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:14]([CH2:13][O:12][C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:5]([OH:25])=[O:4])=[O:24])=[CH:21][CH:20]=1)#[N:23]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 81734983-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester

Produkt 1

HCID 454173003-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acidAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Add lithium hydroxide (0.10 g, 4.18 mmol) to a suspension of 3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester (0.50 g, 1.61 mmol) in a 1:1:1 mixture of water: MeOH: tetrahydrofuran. Stir the mixture at room temperature for 36 h then dilute with water and wash with EtOAc. Adjust the pH of the aqueous phase by the addition of a 1 N solution of hydrochloric acid. Extract the mixture with EtOAc and dry the combined organic phase over anhydrous sodium sulfate. Concentrate under reduced pressure to provide 0.290 g of 3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoic acid as a solid.

Aufarbeitung

  1. washwash with EtOAc
  2. additionby the addition of a 1 N solution of hydrochloric acid
  3. extractionExtract the mixture with EtOAc
  4. dry with materialdry the combined organic phase over anhydrous sodium sulfate
  5. concentrationConcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-23d532fadd6b4f57b0e36ea9c1395946
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079880B2

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