2-Pentyl-1,3-propanediol → 4-(5-Pentyl-1,3-dioxane-2-yl)cyclohexanecarboxylic acid methylester

HRID 1977562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1977562
[CH2:1]([CH:6]([CH2:9][OH:10])[CH2:7][OH:8])[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:11][O:12][C:13]([CH:15]1[CH2:20][CH2:19][CH:18]([CH:21]=O)[CH2:17][CH2:16]1)=[O:14]>C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]([CH:15]1[CH2:20][CH2:19][CH:18]([CH:21]2[O:10][CH2:9][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][O:8]2)[CH2:17][CH2:16]1)=[O:14]

Komponenten

4

Edukt 2

HCID 1175092-Pentyl-1,3-propanediolHCID 11252253Methyl 4-formylcyclohexane-1-carboxylate

Produkt 1

HCID 537639904-(5-Pentyl-1,3-dioxane-2-yl)cyclohexanecarboxylic acid methylesterAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-Pentyl-1,3-propanediol 17.0 g (116 mol) and 4-formylcyclohexane carboxylic acid methyl ester 18.8 g (111 mmol) were dissolved in toluene 120 ml, and PTS 1.0 g was added, and the mixture was refluxed with heating for 3 hours while removing water formed with Dien-Stark. The reactant was washed with a saturated sodium bicarbonate aqueous solution, and then with saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=4/1) to obtain 4-(5-pentyl-1,3-dioxane-2-yl)cyclohexanecarboxylic acid methylester 28.2 g (94.5 mmol). The yield was 85.1% from 4-formylcyclohexanecarboxylic acid methylester.

Aufarbeitung

  1. additionPTS 1.0 g was added
  2. temperaturethe mixture was refluxed
  3. temperaturewith heating for 3 hours
  4. customwhile removing water
  5. customformed with Dien-Stark
  6. washThe reactant was washed with a saturated sodium bicarbonate aqueous solution
  7. dry with materialwith saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-b21a0dc12c194d4cb75fa751f178fb93
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235355B1

Notizen zur Reaktion

Wird geladen…