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Methanol → alpha-Methylthio-alpha-(m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl)propionic acid

HRID 1277786
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1277786
CO.[CH3:3][S:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:21][CH2:20][CH2:19][O:18]2)[CH:12]=1)([CH3:10])[C:6]([O:8]C)=[O:7].[OH-].[Na+]>O>[CH3:3][S:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:21][CH2:20][CH2:19][O:18]2)[CH:12]=1)([CH3:10])[C:6]([OH:8])=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12819455Methyl alpha-methylthio-alpha-[m-(2phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate

Produkt 1

HCID 12819458alpha-Methylthio-alpha-(m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl)propionic acidAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel
2×

Versuchsvorschrift

Methanol (4 ml) and 1 ml of water were added to 1.277 g of methyl α-methylthio-α-[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate. Furthermore, 350 mg of sodium hydroxide was added, and the mixture was heated under reflux for 2 hours. After cooling, 30 ml of water was added, and the mixture was washed twice with 10 ml of diethyl ether. To the aqueous layer was added about 6 ml of 3.5% hydrochloric acid to adjust its pH to 3. It was then extracted four times with 20 ml of diethyl ether. The organic layer was washed twice with 10 ml of water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to afford 1.199 g of α-methylthio-α-[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionic acid as colorless crystals.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. washthe mixture was washed twice with 10 ml of diethyl ether
  5. additionTo the aqueous layer was added about 6 ml of 3.5% hydrochloric acid
  6. extractionIt was then extracted four times with 20 ml of diethyl ether
  7. washThe organic layer was washed twice with 10 ml of water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9b27767a34df4042b446fab802844dd4
Quelldatensatz
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04278802

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