4-Toluenesulfonyl chloride → HCID 19771312, Verbindung

HRID 846032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846032
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH2:4][OH:5].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].C1(NC2CCCCC2)CCCCC1>CC(C)=O>[S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)([O:5][CH2:4][C:3]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=1[CH3:1])(=[O:15])=[O:14]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 7582DicyclohexylamineHCID 12204069(2-Methyl-6-nitrophenyl)methanol

Produkt 1

HCID 19771312HCID 19771312, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

A 100 mL round bottomed flask equipped with a dropping funnel was charged with 2.50 g of 2-methyl-6-nitrobenzyl alcohol and 3.14 g of tosyl chloride dissolved in 30 mL of dry acetone under argon. To the mixture was added dropwise 3.30 mL of dicylohexylamine dissolved in 5 mL of dry acetone while cooling so as to keep the temperature below 15° C. The reaction mixture was brought to room temperature and stirred for 1 day. The mixture was filtered to remove dicyclohexylamine hydrochloride, the solvent removed under vacuum, and the residue chromatographed over silica gel using carbon tetrachloride as the eluent. The product was recrystallized from methylene chloride/pentane to give 1.82 g (38% yield) of white crystals.

Aufarbeitung

  1. customA 100 mL round bottomed flask equipped with a dropping funnel
  2. temperaturewhile cooling so as
  3. customthe temperature below 15° C
  4. customwas brought to room temperature
  5. filtrationThe mixture was filtered
  6. customto remove dicyclohexylamine hydrochloride
  7. customthe solvent removed under vacuum
  8. customthe residue chromatographed over silica gel
  9. customThe product was recrystallized from methylene chloride/pentane

Quellen und Nachweise

ORD-Eintrag
ord-a6031744064947e68f3b36e0be9a9a8c
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05135838

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