Sodium Hydroxide → 8-Acetyl-12-hydroxyheptadec-10-ynoic acid

HRID 1833776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1833776
[C:1]([C:4]([CH2:21][C:22]#[C:23][CH:24]([O:30]C(=O)C)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])C(OCC)=O)(=[O:3])[CH3:2].[OH-].[Na+]>O.CO>[C:1]([CH:4]([CH2:21][C:22]#[C:23][CH:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 20322248Diethyl 2-acetyl-2-(4-acetoxy-2-nonyn-1-yl)azelate

Produkt 1

HCID 203222518-Acetyl-12-hydroxyheptadec-10-ynoic acidAusbeute 36,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of diethyl 2-acetyl-2-(4-acetoxy-2-nonyn-1-yl)azelate (59.7 g., 0.128 mole) and sodium hydroxide (30 g., 0.75 mole) in water (200 ml.) and methanol (800 ml.) is heated at 60° for 16 hours. Most of the methanol is then distilled at reduced pressure and the residue is dissolved in water. The solution is acidified to Congo Red with hydrochloric acid and the oily product taken up in ether and dried over sodium sulfate. Evaporation of the ether leaves 41.1 g. of the crude product as a reddish viscous oil. The product is purified by chromatography on 650 g. of silica gel with 2% methanol in chloroform as eluant. Fifteen grams of pure 8-acetyl-12-hydroxy-10-heptadecynoic acid is obtained as a yellow viscous oil; pmr (CDCl3) δ0.90 (3H,t), 2.20 (3H,s CH3CO), 4.37 (1H,t HCO).

Aufarbeitung

  1. distillationMost of the methanol is then distilled at reduced pressure
  2. dissolutionthe residue is dissolved in water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the ether
  5. customleaves 41.1 g
  6. customThe product is purified by chromatography on 650 g

Quellen und Nachweise

ORD-Eintrag
ord-7cac23ca41d34b91b0551018f0586863
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04066692

Notizen zur Reaktion

Wird geladen…