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Hydrochloric Acid → 3,4-(Dimethylmethylenedioxy)-2-hydroxy-5-hexen-1-yl p-toluenesulfonate

HRID 1741949
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1741949
[CH3:1][C:2]1([CH3:13])[O:12][CH:9]([CH:10]=[CH2:11])[CH:4]([CH:5]([OH:8])[CH2:6][OH:7])[O:3]1.N1C=CC=CC=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>C(Cl)(Cl)Cl>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([O:7][CH2:6][CH:5]([OH:8])[CH:4]2[O:3][C:2]([CH3:13])([CH3:1])[O:12][CH:9]2[CH:10]=[CH2:11])(=[O:28])=[O:27])=[CH:22][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 141882493,4-(Dimethylmethylenedioxy)-5-hexene-1,2-diol

Produkt 1

HCID 190109853,4-(Dimethylmethylenedioxy)-2-hydroxy-5-hexen-1-yl p-toluenesulfonateAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212
Chloroform
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3,4-(Dimethylmethylenedioxy)-5-hexene-1,2-diol (9.77 g) was mixed with 155 ml of pyridine and 52 ml of chloroform, and 11.39 g of p-toluenesulfonyl chloride was added gradually in four portions at 0° C. The mixture was stirred at 0° C. for 6 hours, poured into 6N hydrochloric acid with ice and extracted with diethyl ether. The extract was washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution in sequence, dried with anhydrous ride aqueous solution in sequence, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 17.88 g of 3,4-(dimethylmethylenedioxy)-2-hydroxy-5-hexen-1-yl p-toluenesulfonate having the following properties.

Aufarbeitung

  1. additionwas added gradually in four portions at 0° C
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with a saturated sodium hydrogen carbonate aqueous solution
  4. dry with materiala saturated sodium chloride aqueous solution in sequence, dried with anhydrous ride aqueous solution in sequence
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-865fe2c9ba554b55ad414c429207fb1f
Quelldatensatz
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05334740

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