Sulfuric Acid → Cyclopentanone, 2-(1-hydroxypentyl)-

HRID 1373488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373488
[CH:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+].[C:9]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.S(=O)(=O)(O)O.C[Si].C(OCCOCCO)C>[OH-].[Na+].C(=C1CCCC1=O)CCCC.O>[OH:6][CH:1]([CH:10]1[CH2:11][CH2:12][CH2:13][C:9]1=[O:14])[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

10

Edukt 6

HCID 1118Sulfuric AcidHCID 8063Pentanal2×HCID 8146Diethylene Glycol Monoethyl EtherHCID 8452CyclopentanoneHCID 14797Potassium HydroxideHCID 6328649METHYLSILANE

Produkt 1

HCID 162060Cyclopentanone, 2-(1-hydroxypentyl)-Ausbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14798Sodium HydroxideKatalysatorHCID 860002-PentylidenecyclopentanoneKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Valeraldehyde having an acid value of 3.4 mg-KOH/g was used as the starting material. 117.6 g (1.4 mol) cyclopentanone, 125.2 g water and 2.8 g (0.033 mol) 48% NaOH were introduced into a 500-mL four-necked flask, then the mixture was cooled to 0° C. under stirring, and 72.4 g (0.84 mol) valeraldehyde was added dropwise at the same temperature over 4 hours. Thereafter, the mixture was stirred at the same temperature for 4 hours. After the reaction was finished, the mixture was neutralized with 17.4 g of 10% sulfuric acid and the organic layer was analyzed by gas chromatography. In this analysis, a methyl silicon column was used and diethylene glycol monoethyl ether (carbitol) was added as the standard. The result indicated that the reaction mixture contained 124.4 g (0.73 mol) 2-(1-hydroxy-n-pentyl)cyclopentanone (yield 87.4%) and 2.5 g (0.016 mol) 2-pentylidene cyclopentanone.

Aufarbeitung

  1. stirringThereafter, the mixture was stirred at the same temperature for 4 hours

Quellen und Nachweise

ORD-Eintrag
ord-b3700ef654d04a07ab1fd597d7c92809
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07161041B2

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