3,4-dihydro-2H-pyran → 2H-Pyran, 2-[(5-chloropentyl)oxy]tetrahydro-

HRID 1654295

Reaktionsgleichung

Reaktionsgleichung von HRID 1654295
[CH2:1]([Cl:7])[CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1>CCOCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][Cl:7]

Komponenten

5

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 789155-Chloro-1-pentanol

Produkt 1

HCID 1144672H-Pyran, 2-[(5-chloropentyl)oxy]tetrahydro-Ausbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A stirred solution of pentamethylene chlorohydrin (10.0 g, 0.0816 mol) in Et2O (165 ml) under nitrogen was treated with 3,4-dihydro-2H-pyran (10.3 g, 0.122 mol) and p-toluenesulfonic acid hydrate (0.5 g) and kept at ambient temperature for 4.5 hours. The mixture was washed with aqueous NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was distilled to give 4.06 g, bp 79°-82° C. (0.1-0.07 mm Hg) and 10.54 g, bp 82°-84° C. (0.1-0.07 mm Hg) of 5-chloropentyl 2-tetrahydropyranyl ether.

Aufarbeitung

  1. washThe mixture was washed with aqueous NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. distillationThe residue was distilled

Quellen und Nachweise

ORD-Eintrag
ord-b3eb007816c34156b30dce6d8f04761a
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05405997

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