Sodium Hydroxide → 4-(3-(2,6-Dimethylbenzyloxy)phenyl)butyric acid

HRID 516833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516833
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:9]=[CH:10][CH:11]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66875682Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)butanoate

Produkt 1

HCID 219645274-(3-(2,6-Dimethylbenzyloxy)phenyl)butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)butanoate (Step B, 3.26 g, 10 mmol) in abs ethanol (60 ml) was treated with 1N NaOH (20 ml) at room temperature. The reaction mixture was stirred for 3 hours, or until all the starting material is gone, concentrated and diluted with chloroform and acidified by 1M HCl to bring the pH to 3.5-4. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid) to give the title compound as white solid.

Aufarbeitung

  1. concentrationconcentrated
  2. additiondiluted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-e8d3091c8d1a4b4ca9ff2806576b3bd7
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115072B2

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