Water → 4'-(3-Ethoxy-1,1-dimethyl-3-oxopropyl)-2'-(3-methoxypropoxy)biphenyl-4-carboxylic acid

HRID 1690625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690625
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:23])([CH3:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:5][CH:4]=1)=[O:2].[Mn]([O-])(=O)(=O)=[O:31].[K+].O>CC(C)=O>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][C:15]([C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]([OH:31])=[O:2])=[CH:8][CH:7]=2)=[C:10]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:11]=1)([CH3:23])[CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 86633301Ethyl 3-[4'-formyl-2-(3-methoxypropoxy)biphenyl-4-yl]-3-methylbutanoate

Produkt 1

HCID 669063764'-(3-Ethoxy-1,1-dimethyl-3-oxopropyl)-2'-(3-methoxypropoxy)biphenyl-4-carboxylic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Ethyl 3-[4′-formyl-2-(3-methoxypropoxy)biphenyl-4-yl]-3-methylbutanoate (1.0 g, 2.5 mmol) was dissolved in acetone (40 mL) and a solution of potassium permanganate (1.4 g, 8.8 mmol) and water (20 mL) was added at room temperature. The mixture was stirred for 18 hrs and then filtered. Dichloromethane was added and the mixture was then acidified at 0° C. with HCl 1N. The aqueous layer was extracted three times with dichloromethane and the combined organic layers were washed twice with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 1.0 g, (96%) of the desired product as a brown solid.

Aufarbeitung

  1. filtrationfiltered
  2. additionDichloromethane was added
  3. customwas then acidified at 0° C. with HCl 1N
  4. extractionThe aqueous layer was extracted three times with dichloromethane
  5. washthe combined organic layers were washed twice with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2149c4c965d64492bf1b45583c05e0cb
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153647B2

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