p-Toluenesulfonic acid → 4-[1,3]Dioxan-2-yl-butyric acid methyl ester

HRID 33222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33222
[CH3:1][O:2][CH:3]([O:11][CH3:12])[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[CH2:13](O)CCO.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:10][O:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]1[O:11][CH2:12][CH2:13][CH2:1][O:2]1

Komponenten

7

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 516892Sodium BicarbonateHCID 551444Methyl 5,5-dimethoxyvalerate

Produkt 1

HCID 693128054-[1,3]Dioxan-2-yl-butyric acid methyl esterAusbeute 103,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Methyl 5,5-dimethoxyvalerate (20.0 g, 0.114 mol), propane-1,3-diol (13 g, 0.17 mol) and para-toluene sulphonic acid (2.17 g, 0.0114 mol) were heated under Dean-Stark conditions in toluene (100 ml) for 4 h. The mixture was cooled to room temperature and diluted with diethyl ether (100 ml) and then neutralized with solid sodium bicarbonate. The solid was filtered and the filtrate evaporated to give a pale yellow oil (22.3 g). A 10 g portion of this was then purified by silica gel chromatography (eluent 30% EtOAc:hexane) which gave the title compound as a colourless oil (6.82 g).

Aufarbeitung

  1. filtrationThe solid was filtered
  2. customthe filtrate evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6977855c72854170a3693e7676d59e38
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429579B2

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