Oxygen → 11-(Methylthio)undecanoic acid

HRID 845350

Reaktionsgleichung

Reaktionsgleichung von HRID 845350
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH3:15]I.O=O.[OH-].[Na+]>O.C(O)C>[CH3:15][S:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Komponenten

7

Edukt 4

HCID 977OxygenHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 54350211-Mercaptoundecanoic Acid

Produkt 1

HCID 34898511-(Methylthio)undecanoic acidAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Into a 3-neck round-bottom flask fitted with a condenser and an addition funnel were added 20 g of 11-mercaptoundecanoic acid, 13 g of methyl iodide and 200 mL of ethanol. A slow flow of nitrogen through the reactor was started to exclude oxygen because mercaptans can be converted into disulfides in the presence of air and strong alkali. A solution of 7.33 g of sodium hydroxide in 14.66 g of water was added dropwise to the reaction mixture via the addition funnel. The reaction mixture was kept at room temperature overnight. Any unreacted methyl iodide, the ethanol and the water were removed using a rotovap. The residue was acidified using a mixture of concentrated hydrochloric acid and ice. After isolation the product was distilled. After a small amount of a low boiling fraction was collected, the desired product was collected at ~1 mm of Hg at 180° C. weighing 22.75 g. The crude product was distilled to yield 12.5 g of desired product representing 58.7% of theoretical based upon the weight of starting 11-mercaptoundecanoic acid.

Aufarbeitung

  1. customInto a 3-neck round-bottom flask fitted with a condenser and an addition funnel
  2. customAny unreacted methyl iodide, the ethanol and the water were removed
  3. additiona mixture of concentrated hydrochloric acid and ice
  4. distillationAfter isolation the product was distilled
  5. customAfter a small amount of a low boiling fraction was collected
  6. customthe desired product was collected at ~1 mm of Hg at 180° C.
  7. distillationThe crude product was distilled

Quellen und Nachweise

ORD-Eintrag
ord-bd71a1b903a146d99b276e47e35d669e
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04758369

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