Triethylamine → Benzoic acid, 4-[3-[(methylsulfonyl)oxy]propyl]-, methyl ester

HRID 509899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 509899
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][O:13][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14425137Methyl 4-(3-hydroxypropyl)benzoate

Produkt 1

HCID 10423370Benzoic acid, 4-[3-[(methylsulfonyl)oxy]propyl]-, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

4-(3-Hydroxy-propyl)-benzoic acid methyl ester (1.27 g, 6.5 mmol) and triethylamine (1 ml, 7.1 mmol) are dissolved in dichloromethane (30 ml), cooled to −15° C., methanesulfonylchloride (510 μl, 6.5 mmol) is added and stirred at room temperature for 4 h. The reaction mixture is diluted with dichloromethane, washed with potassiumhydrogensulfoate solution and potassiumcarbonate solution, the organic phase is dried over Na2SO4 and concentrated in vacuo. LC (method F): tR=1.88 min; Mass spectrum (ESP): m/z=295 [M+Na]+.

Aufarbeitung

  1. washwashed with potassiumhydrogensulfoate solution and potassiumcarbonate solution
  2. dry with materialthe organic phase is dried over Na2SO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ea01f834f6724491a8a5256947c0a475
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096548B2

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