p-Toluenesulfonic acid → 2-(6-Chlorohexyloxy)tetrahydro-2H-pyran

HRID 1873486

Reaktionsgleichung

Reaktionsgleichung von HRID 1873486
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1>CCOCC>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][O:20]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 748286-Chloro-1-hexanol

Produkt 1

HCID 3298032-(6-Chlorohexyloxy)tetrahydro-2H-pyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

6-Chlorohexanol (6.85 g, 10 mmol) and p-toluenesulphonic acid (500 mg), were dissolved in dry ether (75 ml) and cooled to 0-5° C. in an ice bath. Dihydropyran (4.3 g, 10 mmol) in dry ether (25 ml) was added dropwise with constant stirring over a 30 minute period. After complete addition, the cooling bath was removed and stirring continued for 16 hours. The solution was extracted with water (50 ml×2), dried (MgSO4), filtered and the solvent evaporated under reduced pressure to leave a pale yellow oil. This oil was shown by 13C NMR spectroscopy to be sufficiently pure to be used without purification in the subsequent reactions. Yield 10.1 g (91%).

Aufarbeitung

  1. additionAfter complete addition
  2. customthe cooling bath was removed
  3. stirringstirring
  4. waitcontinued for 16 hours
  5. extractionThe solution was extracted with water (50 ml×2)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customto leave a pale yellow oil
  10. customto be used without purification in the subsequent reactions

Quellen und Nachweise

ORD-Eintrag
ord-c44d41ab7f514eb2871e2c16584eeb49
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304388B2

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