Texanol → 1-Isobutyryloxy-2,2,4-trimethylpentane-3-yl para-toluenesulfonate

HRID 1632793

Reaktionsgleichung

Reaktionsgleichung von HRID 1632793
[CH3:1][CH:2]([CH3:15])[C:3]([O:5][CH2:6][C:7]([CH3:14])([CH3:13])[CH:8]([OH:12])[CH:9]([CH3:11])[CH3:10])=[O:4].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([O:12][CH:8]([CH:9]([CH3:10])[CH3:11])[C:7]([CH3:14])([CH3:13])[CH2:6][O:5][C:3](=[O:4])[CH:2]([CH3:15])[CH3:1])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 6490TexanolHCID 73974-Toluenesulfonyl chloride

Produkt 1

HCID 204424431-Isobutyryloxy-2,2,4-trimethylpentane-3-yl para-toluenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a one-liter, four-necked, round bottom flask equipped with stirrer, condenser, and thermometer, 200.0 parts of pyridine and 54.0 parts of 3-hydroxy-2,2,4-trimethylpentyl 2-methylpropionate were mixed under a nitrogen blanket and cooled to 0° C. using an ice water bath. To this, 57.0 parts of para-toluenesulfonyl chloride were added in portions over a thirty minute period. The solution was stirred for one hour at 0° C. and then allowed to stand for twenty-four hours at 15° C. The mixture was subsequently poured into one liter of ice water, which was then extracted with 700 parts of methylene chloride. The organic layer was washed successively with cold 6N sulfuric acid (until the water layer was acidic to pH paper); dilute sodium bicarbonate (three times with 500 part-portions); and water (twice with 500 part-portions). It was then dried over sodium sulfate, filtered, and the solvent removed in vacuo to yield the 1-isobutyryloxy-2,2,4-trimethylpentane-3-yl para-toluenesulfonate.

Aufarbeitung

  1. customInto a one-liter, four-necked, round bottom flask equipped with stirrer, condenser
  2. waitto stand for twenty-four hours at 15° C
  3. extractionwas then extracted with 700 parts of methylene chloride
  4. washThe organic layer was washed successively with cold 6N sulfuric acid (until the water layer
  5. dry with materialIt was then dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f666d79b2e014a1fb6acc1135dbe1098
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04477618

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