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

HRID 363518

Reaktionsgleichung

Reaktionsgleichung von HRID 363518
[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-8effe885a6cc489eb381db367714b7e9
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874475

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