Sodium Hydroxide → 12-Hydroxy-8-(methanesulfonyl)heptadecanoic acid

HRID 263000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263000
[CH3:1][S:2]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([O:25]C(=O)C)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])(=[O:4])=[O:3].[OH-].[Na+]>CO>[CH3:1][S:2]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:3])=[O:4]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 21317665Methyl 8-methylsulfonyl-12-acetoxyheptadecanoate

Produkt 1

HCID 2021027912-Hydroxy-8-(methanesulfonyl)heptadecanoic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 8-methylsulfonyl-12-acetoxyheptadecanoate (29.4 g., 0.07 mole) and 20% aqueous sodium hydroxide (70 ml.) in methanol (70 ml.) is stirred at room temperature for 17 hours. The resulting solution is evaporated in vacuo at ~100° C. to an oily residue which is dissolved in water. The aqueous solution is extracted with ether and the organic extract discarded. Then, the aqueous phase is acidified to Congo Red with 6N hydrochloric acid and extracted with ether. The organic extract is washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo at ~100° C. providing crude title compound as a viscous oil (23.6 g., 93%).

Aufarbeitung

  1. customThe resulting solution is evaporated in vacuo at ~100° C. to an oily residue which
  2. dissolutionis dissolved in water
  3. extractionThe aqueous solution is extracted with ether
  4. extractionthe organic extract
  5. extractionextracted with ether
  6. extractionThe organic extract
  7. washis washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo at ~100° C.

Quellen und Nachweise

ORD-Eintrag
ord-e374d7a64b2e4dacb5ddd79d8325f265
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04155908

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