1-Butanesulfonyl chloride → 2-Butanesulfonyloxydodecanoic acid

HRID 1780700

Reaktionsgleichung

Reaktionsgleichung von HRID 1780700
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]([OH:5])=[O:4].[CH2:16]([S:20](Cl)(=[O:22])=[O:21])[CH2:17][CH2:18][CH3:19]>N1C=CC=CC=1>[CH2:16]([S:20]([O:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]([OH:5])=[O:4])(=[O:22])=[O:21])[CH2:17][CH2:18][CH3:19]

Komponenten

4

Edukt 2

HCID 754301-Butanesulfonyl chlorideHCID 97783Hydroxylauric Acid

Produkt 1

HCID 190472202-Butanesulfonyloxydodecanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

2-Hydroxydodecanoic acid (1 g) dissolved in a 10% methanolic hydrochloric acid solution was stirred at room temperature for 1 hour. The mixture was then concentrated and distributed into chloroform and water, and the chloroform layer was washed with a 1% aqueous sodium hydrogen carbonate solution and water, dried with anhydrous sodium sulfate and concentrated to give the methyl ester of 2-hydroxydodecanoic acid (1.02 g). To the methyl ester of 2-hydroxydodecanoic acid dissolved in pyridine (20 ml) was added butanesulfonyl chloride (0.80 g), and the mixture was stirred for 8 hours. Then, the pyridine was removed by distillation, and the residue was distributed into chloroform and water. The chloroform layer was dried with anhydrous sodium sulfate, concentrated and subjected-to chromatography on a silica gel column with an eluent system of n-hexane-ethyl acetate (50:1) to give the methyl ester of 2-butanesulfonyloxydodecanoic acid (1.21 g).

Aufarbeitung

  1. customThen, the pyridine was removed by distillation
  2. dry with materialThe chloroform layer was dried with anhydrous sodium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d865f6537bee4af98d82b0b8f1ae0c5b
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05631238

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