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Sodium Hydroxide → (E)-3-cycloheptyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid

HRID 276186
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 276186
C[O:2][C:3](=[O:23])/[C:4](/[C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1)=[CH:5]/[CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>C(O)C>[CH:6]1(/[CH:5]=[C:4](\[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)/[C:3]([OH:23])=[O:2])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67483512(E)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-acrylic acid methyl ester

Produkt 1

HCID 11174693(E)-3-cycloheptyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acidAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
47.5 °C

Versuchsvorschrift

A solution of (E)-3-cycloheptyl-2-(4-methanesulfonyl-phenyl)-acrylic acid methyl ester (6.01 g, 17.8 mmol) in ethanol (65 mL) was treated with a 1N aqueous sodium hydroxide solution (55 mL). The solution was heated at 45-50° C. for 15 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was concentrated in vacuo to remove ethanol. The residue was diluted with water (100 mL) and extracted with diethyl ether (1×150 mL) to remove any neutral impurities. The aqueous layer was then acidified with a 1N aqueous hydrochloric acid solution, and the resulting acid was extracted into ethyl acetate (2×150 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×150 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford (E)-3-cycloheptyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid (4.99 g, 86%) as a white solid: mp 164-166° C.; EI-HRMS m/e calcd for C17H22O4S (M+H)+322.1239, found 322.1237.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove ethanol
  3. additionThe residue was diluted with water (100 mL)
  4. extractionextracted with diethyl ether (1×150 mL)
  5. customto remove any neutral impurities
  6. extractionthe resulting acid was extracted into ethyl acetate (2×150 mL)
  7. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×150 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-298e2b5f5b5d44aba89f2ffc0bd6dfbe
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06353111B1

Notizen zur Reaktion

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