Sodium Hydroxide → (R)-3-hydroxytetradecanoic acid

HRID 5622

Reaktionsgleichung

Reaktionsgleichung von HRID 5622
[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6]C)=[O:5].O1CCOCC1.[OH-].[Na+]>CO>[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 98349453R-hydroxymyristic acid methyl ester

Produkt 1

HCID 5288266(R)-3-hydroxytetradecanoic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Under nitrogen and while stirring there were added dropwise to a solution of 129.2 g of methyl (R)-3-hydroxytetradecanoate, 1033 ml of dioxan and 122.9 g of 28 percent sodium hydroxide solution. 77.5 ml of methanol were added dropwise to the solution. After stirring for a further 1.5 hours the resulting suspension was filtered and the filter cake was washed with 1000 ml of dioxan and filtered off. The filter cake was adjusted to pH 0 by the addition of 650 ml of 1.5N hydrochloric acid. The suspension was stirred, filtered, the filter cake was washed with 3000 ml of water and the crystals were dried. 119.64 g (98%) of (R)-3-hydroxytetradecanoic acid, m.p. 70.6°-71.4°, were obtained.

Aufarbeitung

  1. stirringAfter stirring for a further 1.5 hours the resulting suspension
  2. filtrationwas filtered
  3. washthe filter cake was washed with 1000 ml of dioxan
  4. filtrationfiltered off
  5. additionThe filter cake was adjusted to pH 0 by the addition of 650 ml of 1.5N hydrochloric acid
  6. stirringThe suspension was stirred
  7. filtrationfiltered
  8. washthe filter cake was washed with 3000 ml of water
  9. customthe crystals were dried

Quellen und Nachweise

ORD-Eintrag
ord-3778de4bf8bd4957a0ab8fe7b5d88d63
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245056

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