Sulfuric Acid → 4-Oxo capric acid

HRID 1197720

Reaktionsgleichung

Reaktionsgleichung von HRID 1197720
C(N(CC)CC)C.[CH:8](=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:16](#N)[CH:17]=[CH2:18].[OH:20]S(O)(=O)=O.[OH-:25].[Na+]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1>[O:25]=[C:11]([CH2:12][CH2:13][CH2:14][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9][C:8]([OH:20])=[O:15]

Komponenten

7

Edukt 5

HCID 1118Sulfuric AcidHCID 7855AcrylonitrileHCID 8130HeptanalHCID 8471TriethylamineHCID 14798Sodium Hydroxide

Produkt 1

HCID 5386474-Oxo capric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideKatalysator

Versuchsvorschrift

Triethylamine (10.1 g, 0.1 mol) is added to a solution of heptanal (11.4 g, 0.1 mol), acrylonitrile (5.31 g, 0.1 mol) and 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride (2.69 g, 0.01 mol) and the mixture stirred for 8 hours. The mixture is poured into 1% H2SO4 (150 ml) and extracted with CHCl3 (4×50 ml). This extract is washed with water, NaCO3 solution, and dried over NaSO4 to yield a brown oil. After distillation, (bp 150-175/0.08 mbar), the colourless oil obtained (9.5 g) is hydrolysed with 2.5M NaOH (100 ml) to yield 4.5 g of 4-oxodecanoic acid as a pale brown semi-solid.

Aufarbeitung

  1. extractionextracted with CHCl3 (4×50 ml)
  2. washThis extract is washed with water, NaCO3 solution
  3. dry with materialdried over NaSO4
  4. customto yield a brown oil
  5. distillationAfter distillation, (bp 150-175/0.08 mbar), the colourless oil
  6. customobtained (9.5 g)

Quellen und Nachweise

ORD-Eintrag
ord-be048bd52f5d441fb962499dbd01bfc6
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05277709

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