Water → omega-Cyclohexyldodecanoic acid

HRID 1720805

Reaktionsgleichung

Reaktionsgleichung von HRID 1720805
[OH2:1].[CH:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>S(=O)(=O)(O)O.CC(C)=O>[CH:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:1])=[O:20])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

5

Edukt 2

HCID 962WaterHCID 1487778512-Cyclohexyldodecanol

Produkt 1

HCID 193525omega-Cyclohexyldodecanoic acidAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

CrO3 (VI) (3.204 g, 32.04 mM) was dissolved in sulfuric acid (2.76 ml), followed by stirring for a time, and then water (4.8 ml) was added to yield a solution. This solution was added drop by drop to a solution of 12-cyclohexyldodecanol (5.36 g, 20 mM) in acetone (300 ml) under ice cooling conditions, followed by stirring for 1 hour. To the mixture, iso-prapanol (about 2 ml) was added and then concentrated to dryness under reduced pressure. To the resulting residue, water (50 ml) and chloroform (50 ml) were added, followed by vigorous stirring, after which the chloroform layer was separated. The chloroform layer was dryed over anhydrous sodium sulfate, purified by silica gel colum (50 g) (methanol-chloroform (1:49)) to yield the title compound (5.3 g, yield 58.7%) as a colorless powder.

Aufarbeitung

  1. customto yield a solution
  2. stirringby stirring for 1 hour
  3. additionTo the mixture, iso-prapanol (about 2 ml) was added
  4. concentrationconcentrated to dryness under reduced pressure
  5. additionTo the resulting residue, water (50 ml) and chloroform (50 ml) were added
  6. customafter which the chloroform layer was separated
  7. custompurified by silica gel colum (50 g) (methanol-chloroform (1:49))

Quellen und Nachweise

ORD-Eintrag
ord-c215d465787f42319d335885df261e62
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506267

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